[ CAS No. 73930-39-9 ] {[proInfo.proName]}

Name: 73930-39-9|1-Phenylcyclopropanamine hydrochloride|97%
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Quality Control of [ 73930-39-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 73930-39-9 ]

SDS Specification

Alternatived Products of [ 73930-39-9 ]

Product Details of [ 73930-39-9 ]

CAS No. :	73930-39-9	MDL No. :	MFCD07995722
Formula :	C₉H₁₂ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ABUWJOHYZALSMF-UHFFFAOYSA-N
M.W :	169.65	Pubchem ID :	194548
Synonyms :

Calculated chemistry of [ 73930-39-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.46
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.93
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.22
Consensus Log Po/w :	1.7

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.45
Solubility :	0.608 mg/ml ; 0.00359 mol/l
Class :	Soluble
Log S (Ali) :	-2.1
Solubility :	1.35 mg/ml ; 0.00794 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.82
Solubility :	0.256 mg/ml ; 0.00151 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 73930-39-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 73930-39-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 73930-39-9 ]
Downstream synthetic route of [ 73930-39-9 ]

[ 73930-39-9 ] Synthesis Path-Upstream 1~7

1
[ 6120-95-2 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium azide; sulfuric acid In chloroform	1-Phenylcyclopropa ne carboxylic acid(1) is reacted with sodium azide and sulfuric acid in CHCl3 to yield 1-phenylcyclopropanamine (2). 1-Phenylcyclopropanamine is then reacted with 2-mesitylenesulfonyl chloride in chloroform under basic conditions to yield the protected derivative (3), N-(I- phenylcyclopropyl)mesitylenesulfonamide. N-(I- phenylcyclopropyl)mesitylenesulfonamide (3) is then reacted with N-(4- bromobutyl)phthalimide (4) in DMF with sodium hydride at room temperature overnight, to yield N-(2-mesitylenesulfonyl)-N-(l-phenylcyclopropyl)-4- phthalimidobutylamine (5).[0092] The phthaloyl group is removed from N-(2-mesitylenesulfonyi)-N-(l- phenylcyclopropyl)-4-phthalimidobutylamine (5) by reaction with hydroxylamine hydrochloride in benzene and sodium methoxide in methanol, to produce N-(4- aminobutyl)-N-(l-phenylcyclopropyl)-2-mesitylenesulfonamide (6). The free amino group is then re-protected with 2-mesitylenesulfonyl chloride in 2N NaOH in CHCl3 to give (7), N-(4-(mesitylene-2-sulfonylamino)butyl)-N-(l-phenylcyclopropyl)~2- mesitylenesulfonamide. (7) is then reacted with l,2-bis(mesitylene-2- --> sulfonyloxymethyl)cyclopropane (8) in DMF with sodium hydride at room temperature overnight to yield (9), the tetra-mesitylene-2-sulfonyl- protected derivative of l,2-bis((N-(l-phenylcyclopropyl)-4- aminobutyl)aminomethyl)cyclopropane. The mesitylene protecting groups are then removed using HBr in acetic acid and phenol in methylene chloride to yield 1,2- bis((N-(l-phenylcyclopropyl)-4-aminobutyl)aminomethyl)cyclopropane (CGC-11255; SL-11255).
51%	Stage #1: With diphenyl phosphoryl azide; triethylamine In toluene for 0.75 h; Reflux Stage #2: With ammonium chloride In water; toluene	INTERMEDIATE PREPARATION 31 -phenylcyclop hydrochloride.bul.HCITo a solution of 1-phenylcyclopropanecarboxylic acid (8.80 g, 54.3 mmol) in toluene (260 mL) was added diphenylphosphoryl azide (12.12 mL, 56.2 mmol) and Et₃N (8.94 mL, 64.1 mmol). The mixture was heated to reflux for 45 min, cooled to room temperature, and quenched with saturated aqueous NH₄CI (860 mL). The two phases were separated and the aqueous phase extracted with Et₂0 (3 x 400 mL). The combined ethereal extracts were washed with brine, dried over MgS0₄, filtered and concentrated in vacuo to provide the isocyanate as oil. This material was dissolved in Et₂0 (40 ml.) and concentrated HCI (30 ml.) was added. The resulting mixture was heated on a steam bath for 30 min. Acetone (100 ml.) was added to the mixture and the precipitate was isolated by filtration to provide 1- phenylcyclopropanamine (4.68 g, 51 percent) as the hydrochloride salt. ¹H NMR (400 MHz, DMSO-de) δ 9.01 (br. s., 3H), 7.37 - 7.48 (m, 4H), 7.30 - 7.37 (m, 1 H), 1 .38 - 1.46 (m, 2H), 1.14 - 1.21 (m, 2H); MS (m/z) 133.8 (M+H⁺).

Reference： [1] Patent: WO2006/86773, 2006, A2, . Location in patent: Page/Page column 32-34
[2] Patent: WO2011/119704, 2011, A1, . Location in patent: Page/Page column 35-36
[3] Synthetic Communications, 1980, vol. 10, # 2, p. 107 - 110

2
[ 925-90-6 ]
[ 100-47-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
143 g	Stage #1: With titanium(IV) isopropylate In tert-butyl methyl ether at -10 - 20℃; for 2 h; Inert atmosphere; Large scale Stage #2: With boron trifluoride diethyl etherate In tert-butyl methyl ether at 15 - 20℃; Large scale	Example 4 Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) Synthesis of Intermediate 2 A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄ (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5° C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5° C. The reaction mixture was allowed to warm to 15-20° C. for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15° C. The reaction mixture was stirred at 15-20° C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30° C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30° C. The reaction mixture was extracted with MTBE (3 L2) and EtOAc (3 L2), and the combined organic layers were dried with anhydrous Na₂SO₄ and concentrated under reduced pressure (below 45° C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g	Stage #1: With titanium(IV) isopropylate In tert-butyl methyl ether at -10 - 20℃; for 2 h; Inert atmosphere Stage #2: at 15 - 20℃;	Synthesis of Intermediate 2 A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄ (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5° C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5° C. The reaction mixture was allowed to warm to 15-20° C. for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15° C. The reaction mixture was stirred at 15-20° C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30° C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30° C. The reaction mixture was extracted with MTBE (3 L2) and EtOAc (3 L2), and the combined organic layers were dried with anhydrous Na₂SO₄ and concentrated under reduced pressure (below 45° C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g	Stage #1: With titanium(IV) isopropylate In tert-butyl methyl ether at -10 - 20℃; for 2 h; Inert atmosphere Stage #2: With boron trifluoride diethyl etherate In tert-butyl methyl ether at 15 - 20℃; Inert atmosphere Stage #3: With hydrogenchloride In tert-butyl methyl ether at 30℃; Inert atmosphere	Synthesis of Intermediate 2: A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄ (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to - 5 °C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 °C. The reaction mixture was allowed to warm to 15-20 °C for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 °C. The reaction mixture was stirred at 15-20 °C for 1-2 hr. and stopped when a low level of benzonitrile remained. IN HC1 (2500 ml) was added dropwise while maintaining the inner temperature below 30 °C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 °C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na₂S0₄ and concentrated under reduced pressure (below 45 °C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.

143 g	Stage #1: With titanium(IV) isopropylate In tert-butyl methyl ether at -10 - 20℃; for 2 h; Inert atmosphere Stage #2: With boron trifluoride diethyl etherate In tert-butyl methyl ether at 15 - 20℃; Inert atmosphere Stage #3: With hydrogenchloride In tert-butyl methyl ether	0118] A solution of intermediate 1, benzonitrile, (250 g, 1.0 equiv), and Ti(OiPr)4 (1330 mL, 1.5 equiv.) in MBTE (3750 mL) was cooled to about -10 to -5°C under a nitrogen atmosphere. EtMgBr (1610 mL, 3.0 M, 2.3 equiv) was added dropwise over a period of 60 min, during which the inner temperature of the reaction was kept below 5°C. The reaction mixture was allowed to warm to 15-20°C for 1 hr. BF3-ether (1300 mL, 2.0 equiv) was added dropwise over a period of 60 min, while the inner temperature was maintained below 15°C. The reaction mixture was stirred at 15-20°C for 1-2 hr and stopped when a low level of benzonitrile remained. 1N HCl (2500 mL) was added dropwise while maintaining the inner temperature below 30°C. NaOH (20percent, 3000 mL) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30°C. The reaction mixture was extracted with MTBE (3L x 2) and EtOAc (3L x 2) and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45°C) to yield a red oil. MTBE (2500 mL) was added to the oil to give a clear solution and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of intermediate 2.
143 g	Stage #1: With titanium(IV) isopropylate In tert-butyl methyl ether; benzonitrile at -10 - 20℃; for 2 h; Inert atmosphere Stage #2: With boron trifluoride diethyl etherate In tert-butyl methyl ether; benzonitrile at 15 - 20℃; Stage #3: With hydrogenchloride In tert-butyl methyl ether; water; benzonitrile at 30℃;	A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄ (1330 ml, 1.5 equiv.) in MTBE (3750 ml) was cooled to about -10 to -5 °C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 °C. The reaction mixture was allowed to warm to 15-20 °C for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 °C. The reaction mixture was stirred at 15-20 °C for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 °C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 °C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na₂SO₄ and concentrated under reduced pressure (below 45 °C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.

Reference： [1] Patent: US2015/105358, 2015, A1, . Location in patent: Paragraph 0411
[2] Patent: US2015/150871, 2015, A1, . Location in patent: Paragraph 0269
[3] Patent: WO2016/7423, 2016, A1, . Location in patent: Page/Page column 41; 42
[4] Patent: WO2016/90230, 2016, A1, . Location in patent: Page/Page column 19-20
[5] Patent: US2017/114023, 2017, A1, . Location in patent: Paragraph 0117; 0118
[6] Patent: WO2017/143237, 2017, A1, . Location in patent: Page/Page column 53; 54
[7] Patent: WO2017/214565, 2017, A1, . Location in patent: Page/Page column 38

3
[ 100-47-0 ]
[ 73930-39-9 ]

Reference： [1] Patent: US2015/99744, 2015, A1,
[2] Patent: US2015/105409, 2015, A1,
[3] Patent: US2015/105383, 2015, A1,
[4] Patent: WO2016/87950, 2016, A1, . Location in patent: Page/Page column 30

4
[ 41049-53-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
143 g	With hydrogenchloride In tert-butyl methyl ether	[0251] A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄(1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about −10 to −5° C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5° C. The reaction mixture was allowed to warm to 15-20° C. for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15° C. The reaction mixture was stirred at 15-20° C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30° C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30° C. The reaction mixture was extracted with MTBE (3 L×2) and EtOAc (3 L×2), and the combined organic layers were dried with anhydrous Na₂SO₄and concentrated under reduced pressure (below 45° C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g	With hydrogenchloride In tert-butyl methyl ether	A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄(1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about −10 to −5° C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5° C. The reaction mixture was allowed to warm to 15-20° C. for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15° C. The reaction mixture was stirred at 15-20° C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30° C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30° C. The reaction mixture was extracted with MTBE (3 L×2) and EtOAc (3 L×2), and the combined organic layers were dried with anhydrous Na₂SO₄and concentrated under reduced pressure (below 45° C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g	With hydrogenchloride In tert-butyl methyl ether	A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄ (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5° C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5° C. The reaction mixture was allowed to warm to 15-20° C. for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15° C. The reaction mixture was stirred at 15-20° C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30° C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30° C. The reaction mixture was extracted with MTBE (32) and EtOAc (32), and the combined organic layers were dried with anhydrous Na₂SO₄ and concentrated under reduced pressure (below 45° C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.

Reference： [1] Patent: US2015/99744, 2015, A1, . Location in patent: Paragraph 0251
[2] Patent: US2015/105409, 2015, A1, . Location in patent: Paragraph 0217-0219
[3] Patent: US2015/105383, 2015, A1, . Location in patent: Paragraph 0230-0231

5
[ 75-16-1 ]
[ 100-47-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
143 g	Stage #1: With titanium(IV) isopropylate In tert-butyl methyl ether at 10 - 20℃; for 2 h; Inert atmosphere Stage #2: With boron trifluoride diethyl etherate In tert-butyl methyl ether at 15 - 20℃; Stage #3: With hydrogenchloride In tert-butyl methyl ether; water at 30℃;	A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)₄ (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to - 5 °C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 °C. The reaction mixture was allowed to warm to 15-20 °C for 1 hr. BF₃-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 °C. The reaction mixture was stirred at 15-20 °C for 1-2 hr. and stopped when a low level of benzonitrile remained. IN HC1 (2500 ml) was added dropwise while maintaining the inner temperature below 30 °C. NaOH (20percent, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 °C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na₂S0₄ and concentrated under reduced pressure (below 45 °C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2

Reference： [1] Patent: WO2017/184774, 2017, A1, . Location in patent: Page/Page column 48

6
[ 7647-01-0 ]
[ 6120-95-2 ]
[ 73930-39-9 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 549 - 554

7
[ 63201-02-5 ]
[ 73930-39-9 ]

Reference： [1] Synthetic Communications, 1980, vol. 10, # 2, p. 107 - 110

[ 73930-39-9 ] Synthesis Path-Downstream 1~68

1
[ 63201-02-5 ]
[ 73930-39-9 ]

Reference： [1]Synthetic Communications,1980,vol. 10,p. 107 - 110

2
[ 73930-39-9 ]
[ 279215-55-3 ]
(2-chloro-7,7-dioxo-4,7-dihydro-1,7λ⁶-dithia-4,6-diaza-inden-5-yl)-(1-phenyl-cyclopropyl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4127 - 4139

3
[ 6120-95-2 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium azide; sulfuric acid; In chloroform;	1-Phenylcyclopropa ne carboxylic acid(1) is reacted with sodium azide and sulfuric acid in CHCl3 to yield 1-phenylcyclopropanamine (2). 1-Phenylcyclopropanamine is then reacted with 2-mesitylenesulfonyl chloride in chloroform under basic conditions to yield the protected derivative (3), N-(I- phenylcyclopropyl)mesitylenesulfonamide. N-(I- phenylcyclopropyl)mesitylenesulfonamide (3) is then reacted with N-(4- bromobutyl)phthalimide (4) in DMF with sodium hydride at room temperature overnight, to yield N-(2-mesitylenesulfonyl)-N-(l-phenylcyclopropyl)-4- phthalimidobutylamine (5).[0092] The phthaloyl group is removed from N-(2-mesitylenesulfonyi)-N-(l- phenylcyclopropyl)-4-phthalimidobutylamine (5) by reaction with hydroxylamine hydrochloride in benzene and sodium methoxide in methanol, to produce N-(4- aminobutyl)-N-(l-phenylcyclopropyl)-2-mesitylenesulfonamide (6). The free amino group is then re-protected with 2-mesitylenesulfonyl chloride in 2N NaOH in CHCl3 to give (7), N-(4-(mesitylene-2-sulfonylamino)butyl)-N-(l-phenylcyclopropyl)~2- mesitylenesulfonamide. (7) is then reacted with l,2-bis(mesitylene-2- --> sulfonyloxymethyl)cyclopropane (8) in DMF with sodium hydride at room temperature overnight to yield (9), the tetra-mesitylene-2-sulfonyl- protected derivative of l,2-bis((N-(l-phenylcyclopropyl)-4- aminobutyl)aminomethyl)cyclopropane. The mesitylene protecting groups are then removed using HBr in acetic acid and phenol in methylene chloride to yield 1,2- bis((N-(l-phenylcyclopropyl)-4-aminobutyl)aminomethyl)cyclopropane (CGC-11255; SL-11255).
51%		INTERMEDIATE PREPARATION 31 -phenylcyclop hydrochloride?HCITo a solution of 1-phenylcyclopropanecarboxylic acid (8.80 g, 54.3 mmol) in toluene (260 mL) was added diphenylphosphoryl azide (12.12 mL, 56.2 mmol) and Et3N (8.94 mL, 64.1 mmol). The mixture was heated to reflux for 45 min, cooled to room temperature, and quenched with saturated aqueous NH4CI (860 mL). The two phases were separated and the aqueous phase extracted with Et20 (3 x 400 mL). The combined ethereal extracts were washed with brine, dried over MgS04, filtered and concentrated in vacuo to provide the isocyanate as oil. This material was dissolved in Et20 (40 ml.) and concentrated HCI (30 ml.) was added. The resulting mixture was heated on a steam bath for 30 min. Acetone (100 ml.) was added to the mixture and the precipitate was isolated by filtration to provide 1- phenylcyclopropanamine (4.68 g, 51 %) as the hydrochloride salt. 1H NMR (400 MHz, DMSO-de) delta 9.01 (br. s., 3H), 7.37 - 7.48 (m, 4H), 7.30 - 7.37 (m, 1 H), 1 .38 - 1.46 (m, 2H), 1.14 - 1.21 (m, 2H); MS (m/z) 133.8 (M+H+).

Reference： [1]Patent: WO2006/86773,2006,A2 .Location in patent: Page/Page column 32-34
[2]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 35-36
[3]Synthetic Communications,1980,vol. 10,p. 107 - 110
[4]ChemMedChem,2020,vol. 15,p. 643 - 658

4
[ 773-64-8 ]
[ 73930-39-9 ]
[ 905912-11-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium hydroxide; In chloroform;	1-Phenylcyclopropa ne carboxylic acid(1) is reacted with sodium azide and sulfuric acid in CHCl3 to yield 1-phenylcyclopropanamine (2). 1-Phenylcyclopropanamine is then reacted with 2-mesitylenesulfonyl chloride in chloroform under basic conditions to yield the protected derivative (3), N-(I- phenylcyclopropyl)mesitylenesulfonamide. N-(I- phenylcyclopropyl)mesitylenesulfonamide (3) is then reacted with N-(4- bromobutyl)phthalimide (4) in DMF with sodium hydride at room temperature overnight, to yield N-(2-mesitylenesulfonyl)-N-(l-phenylcyclopropyl)-4- phthalimidobutylamine (5).[0092] The phthaloyl group is removed from N-(2-mesitylenesulfonyi)-N-(l- phenylcyclopropyl)-4-phthalimidobutylamine (5) by reaction with hydroxylamine hydrochloride in benzene and sodium methoxide in methanol, to produce N-(4- aminobutyl)-N-(l-phenylcyclopropyl)-2-mesitylenesulfonamide (6). The free amino group is then re-protected with 2-mesitylenesulfonyl chloride in 2N NaOH in CHCl3 to give (7), N-(4-(mesitylene-2-sulfonylamino)butyl)-N-(l-phenylcyclopropyl)~2- mesitylenesulfonamide. (7) is then reacted with l,2-bis(mesitylene-2- --> sulfonyloxymethyl)cyclopropane (8) in DMF with sodium hydride at room temperature overnight to yield (9), the tetra-mesitylene-2-sulfonyl- protected derivative of l,2-bis((N-(l-phenylcyclopropyl)-4- aminobutyl)aminomethyl)cyclopropane. The mesitylene protecting groups are then removed using HBr in acetic acid and phenol in methylene chloride to yield 1,2- bis((N-(l-phenylcyclopropyl)-4-aminobutyl)aminomethyl)cyclopropane (CGC-11255; SL-11255).

Reference： [1]Patent: WO2006/86773,2006,A2 .Location in patent: Page/Page column 32-34

5
[ 1215106-60-7 ]
[ 73930-39-9 ]
[ 1215105-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	4-fluoro-2-(4-fluorophenyl)-N-methyl-5-(2-methyl-5-(l- phenylcyclopropyIcarbamoyl)phenyl)pyrazoIo[l,5-a]pyridine-3-carboxamide.To a solution containing <strong>[73930-39-9]1-phenylcyclopropanamine hydrochloride</strong> (0.030 g, 0.18 mmol), diisopropylethylamine (0.16 niL, 0.95 mmol), 3-(4-fiuoro-2-(4- fluorophenyl)-3 -(methylcarbamoyl)pyrazolo [1,5 -a]pyridin- 5 -yl)-4-methylb enzoic acid (0.050 g, 0.12 mmol) and DMF (0.8 mL) was added HATU (0.09 g, 0.24 mmol) in one portion. The solution was maintained at room temperature for Ih and concentrated. The resultant residue was purified using preparative HPLC (Waters- Xbridge, 50 x 100 mm, 5 micron, Cl 8 column; 0.1M ammonium acetate, 10-100% B (B = 5% H2O/CH3CN)/ A (A = 95% H2O/ CH3CN), 15 min. gradient) to afford 4- fluoro-2-(4-fluorophenyl)-N-memyl-5-(2-methyl-5-(l- phenylcyclopropylcarbamoyl)rhohenyl)pyrazolo[ 1 ,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC retention time: 9.0 min. IH NMR (400 MHz, CHLOROFORM-^ delta ppm 8.35 (d, ./=6.78 Hz, 1 H), 7.81 - 7.90 (m, 2 H), 7.76 (d, J=7.78 Hz, 1 H)5 7.72 (s, 1 H), 7.40 (d, J-8.03 Hz, 1 H), 7.29 - 7.37 (m, 4 H), 7.13 - 7.24 (m, 3 H), 6.90 (s, 1 H), 6.73 (t, J=6.65 Hz5 1 H), 5.90 (d, J=4.52 Hz, 1 H), 2.97 (d, J=4.77 Hz, 3 H), 2.32 (s, 3 H), 1.39 (br. s., 4 H). LCMS retention time: 1.975 min. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Xbridge, 5 micron, C18, 4.6 x 50 mm column using a SPD-10AV UV- Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 5% CH3CN / 95% H2O / 10 mM ammonium acetate and solvent B was 5% H2O / 95% CH3CN / 10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 537 (MH+).

Reference： [1]Patent: WO2010/30538,2010,A2 .Location in patent: Page/Page column 129-130

6
[ 1215107-53-1 ]
[ 73930-39-9 ]
[ 1215105-25-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	4-flalphaoro-5-(3-fluoro-2-methyl-S-(l~phenylcyclopropyIcarbamoyl)phenyl)-2-(4- fluorophenyl)~N-methylpyrazolo[l,5-a]pyridine-3-carboxamide. To a solution containing <strong>[73930-39-9]1-phenylcyclopropanamine hydrochloride</strong> (0.059 g, 0,027 mmol), diisopropylethylamine (0.04 mL, 0.22 mmol), 3-fluoro-5-(4-fluoro-2-(4- fluororhohenyl)-3-(methylcarbamoyl)pyrazolo[l,5-a]pyridin-5-yl)-4-methylbenzoic acid (0.012 g, 0.027 mmol) and DMF (0.19 mL) was added HATU (0.021 g, 0.055 mmol) in one portion. The solution was maintained at room temperature for Ih and concentrated. The resultant residue was purified using preparative HPLC (Waters- Xbridge, 50 x 100 mm, 5 micron, Cl 8 column; 0.1M ammonium acetate, 0-100% B (B = 5% H2O/CH3CN)/ A (A = 95% H2O/ CH3CN), 20 min. gradient) afforded 4- fluoro-5-(3-fluoro-2-methyl-5-(l-phenylcycloprorhoylcarbamoyl)phenyl)-2-(4- fluorophenyl)-N-methylpyrazolo[l,5-a]pyridine-3-carboxamide as a white solid. Preparative HPLC retention time: 15.0 min. 1 H NMR (400 MHz1 CHLOROFORM- d) delta ppm 8.36 (d, J-7.03 Hz, 1 H), 7.80 - 7.89 (m, 2 H), 7.56 (d, J=9.79 Hz, 1 H), 7.51 (s, 1 H), 7.28 - 7.36 (m, 4 H), 7,13 - 7.25 (m, 3 H), 6.91 (s, 1 H), 6.72 (t, /=6.78 Hz, 1 H), 5.85 (d, J=4.27 Hz, 1 H), 2.97 (d, J=4.77 Hz, 3 H), 2.23 (s, 3 H)5 1.38 (s, 4 H). LCMS retention time: 2,437 min. LC data was recorded on a Shimadzu LC- IOAS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 3.0 x 50 mm column using a SPD-10AV UV- Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3OH / 90% H2O / 10 mM TFA and solvent B was 10% H2O / 90% CH3OH / 10 niM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 555 (MH+).

Reference： [1]Patent: WO2010/30538,2010,A2 .Location in patent: Page/Page column 132

7
[ 1215106-65-2 ]
[ 73930-39-9 ]
[ 1215106-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	Tert-butyl 7-fluoro-2-(4-fluorophenyl)~5-(2-methyl-5-(l-phenylcyclopropyl carbamoy^phenyOpyrazolotl^-alpyridine-S-carbonyltmethylJcarbaraate. To a solution containing l-phenylcyclopropanamine hydrochloride (0.010 g, 0.061 mmol), diisopropylethylamine (0,086 mL, 0.49 mmol), 3-(3-(tert- butoxycarbonyl(methyl)carbamoyl)-7-fluoro-2-(4-fluorophenyl)pyrazolo[l,5- a]pyridin-5-yl)-4-methylbenzoic acid (0.032 g> 0.061 mmol) and DMF (0.41 mL) was added HATU (0.047 g, 0.12 mmol) in one portion. The solution was maintained at room temperature for Ih and concentrated. The resultant residue was purified on silica gel (30-100% ethyl acetate/hexanes, 45 min. gradient) to afford tert-butyl 7- fluoro-2-(4-fluorophenyl)-5-(2-rnethy-5-(l- phenylcyclopropylcarbamoyl)phenyl)pyrazolo [1,5 -a]pyridine-3 - carbonyl(methyl)carbamate as a residue. LCMS retention time: 2.938 min. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 3.0 x 50 mm column using a SPD-10AV UV- Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3OH / 90% H2O / 10 mM TFA and solvent B was 10% H2O / 90% CH3OH / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 637 (MH+).

Reference： [1]Patent: WO2010/30538,2010,A2 .Location in patent: Page/Page column 149

8
[ 1215106-70-9 ]
[ 73930-39-9 ]
[ 1215106-88-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	2-(4-fluorophenyl)-N-methyl-5-(3-(l- phenylcyclopropylcarbamoyOpheny^furoIljS-blpyridine-S-carboxaniide. Step 1 Preparation of 3-(3-broitauio-2-(4-fluorophenyl)furo[2,3~b]pyridin-5-yl)-N-(l - phenylcyclopropyl)benzamide. DIEA (286 muL, 1.64 mmol) was added to a stirring solution of HATU (311 mg, 0.819 mmol), 1-phenylcycloprorhoanamine hydrochloride (111 mg, 0.655 mmol), and 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5- yljbenzoic acid (225 mg, 0.546 mmol) in DMF (6 inL) at room temperature. It was allowed to stir for 1 hour. The mixture was diluted with EtOAc and washed with IM HCl, and sat NaCL The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product 3-(3-bromo-2-(4-fluorophenyl)furo[2,3- b]pyridin-5-yl)-N--(l-phenylcyclopropyl)benzamide (180 mg, 0.341 mmol, 63 % yield) consistent by LCMS. LC-MS retention time: 1.89 min; m/z (MH+): 529. LC data was recorded on a Shimadzu LC-IOAS liquid chroralphaatograph equipped with a Waters XBridge 5u C18 4.6x50mm column using a SPD-IOAV UV- Vis detector at a detector wave length of 22OnM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetom'trile / 95% H2O / 10 mM ammonium acetate and solvent B was 5% H2O / 95% acetonitrile / 10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Reference： [1]Patent: WO2010/30538,2010,A2 .Location in patent: Page/Page column 168-169

9
[ 1215104-90-7 ]
[ 73930-39-9 ]
[ 1215104-93-0 ]

Yield	Reaction Conditions	Operation in experiment
28%	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	2-(4-Fluorophenyl)-N-methyl-6-(3-(l~ phenylcyclopropylcarbamoyI)phenyl)imidazo[l,2-a]pyridine-3-carboxamide. 3-(2-(4-Fluororhohenyl)-3-(niethylcarbamoyl)imidazo[l,2~a]pyridin-6-yl)benzoic acid (40 mg, 0.10 mmol) and l-phenylcyclopropaiiamine, HCl (26 mg, 0.15 mmol) were slurried into DMF (0.7 mL) and TEA (0.1 mL), HATU (59 mg, 0.15 mmol) was added to this slurry (solution became yellow). The reaction was stirred at rt for 2 hrs (complete by LCMS). The reaction was diluted with MeOH (0.7 mL), filtered and purified by prep HPLC (acetonitrile/water, with 10 mM ammom'un acetate buffer) to yield 2-(4-fluorophenyl)-N-methyl-6-(3 -( 1 - phenylcycloprorhoylcarbamoyl)phenyl)imidazo[l,2-a]pyridine-3-carboxamide (15.2 mg, 0.028 mmol, 28% yield) as a white solid. 1H NMR (500 MHz, CD3OD) deltappm 9.27 (br s, IH), 8.31 (br s, IH), 7.97 - 7.88 (m 3H), 7.82 - 7.76 (m, 3H), 7.66 (t, J = 7.8 Hz, IH), 7.35 - 7.26 (m, 6H), 7.22 - 7.17 (m, IH), 2.90 (s, 3H), 1.45 - 1.36 (m, 4H). LC-MS retention time 1.63 rnin; m/z 505 (MH+). LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Phenomenex-Luna 1Ou Cl 8 3.0x50mm column using a SPD-10AV UV- Vis detector at a detector wave length of 22OnM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 10% acetonitrile / 90% H2O / 0.1% TFA and solvent B was 10% H2O / 90% acetonitrile / 0.1% TFA. MS data was determined using a Micromass Platform for LC in electrospray mode.

Reference： [1]Patent: WO2010/30538,2010,A2 .Location in patent: Page/Page column 97

10
[ 70097-69-7 ]
[ 73930-39-9 ]
C₁₆H₁₄ClN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol;	Example 15 5-chloro-2-imino-1-(1-phenylcyclopropyl)-1,2-dihydropyridine-3-carboxamide To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.5 g) in methanol (10 ml) was added a solution of <strong>[73930-39-9]1-phenylcyclopropylamine hydrochloride</strong> (1.1 g) and triethylamine (0.89 ml) in methanol (5 ml) at room temperature, and the mixture was stirred overnight at 50C. The solvent was evaporated under reduced pressure, acetic acid (5 ml) was added, and the mixture was stirred at 50C for 2 hr. The solvent was evaporated under reduced pressure, the residue was partitioned with ethyl acetate and aqueous sodium bicarbonate, and the organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3?1:0). The obtained yellow oil was purified by preparative HPLC, and the obtained fraction was treated with PL-HCO3 MP (200 mg cartridge, Polymer Laboratory) to give the title compound (2.5 mg). 1H NMR (300 MHz, CDCl3) delta ppm 1.03-2.15 (4 H, m), 5.86 (1 H, br. s.), 6.92 (2 H, d, J=7.2 Hz), 7.29-7.50 (4 H, m), 8.26 (1 H, d, J=2.7 Hz), 10.98 (1 H, br. s.).

Reference： [1]Patent: EP2269989,2011,A1 .Location in patent: Page/Page column 41

11
[ 1217339-52-0 ]
[ 73930-39-9 ]
[ 1217336-73-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	To a 50mL RBF was added 3-(2-(4- fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methoxybenzoic acid (433.9 mg, 1.035 mmol), DMF (15 mL), 1-phenylcyclopropan- amine, HC1 (214 mg, 1.259 mmol), N-ethyl-N-isopropylpropan-2-amine (0.438 mL, 2.52 mmol), and finally HATU, 2-(3 H- [ 1 ,2,3 ]triazolo [4,5-b]pyridin-3 -yl)- 1 , 1 ,3 ,3 -tetramethylisouronium hexafluorophosphate(V) (1180 mg, 3.10 mmol)). The mixture was stirred over night at room temperature. The reaction mixture was diluted with dichloromethane, washed with 0.5M HC1, then brine and dried over MgS04. The solution was concentrated to give a tan oil. The crude product was taken up in lOmL of acetonitrile and purified using a Shimadzu preparative HPLC employingacetonitrile/water/0.1%TFA where solvent A was 10% acetonitrile / 90% H20/ 0.1% trifluoroacetic acid and solvent B was 10% H20 / 90% acetonitrile/ 0.1%trifluoroacetic acid with a Phenomenex-Luna IotaOmicronmuiotaeta CI 8 30 x 100mm column at a gradient of 40-100% B and a flow rate of 40 mL/min. over 8 minutes with a 12 minute hold to give a 77% yield of product as a white powder. The LC/MS data was obtained on a Shimadzu analytical LC /Micromass Platform LC (ESI+) at 220nm using the following set of conditions: Waters Sunfire 5muetaiota CI 8, 4.6 x 50mm column, with a gradient of 0-100%B (B = 90% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 10% HPLC grade water), (A = 90% HPLC grade water / 0.1% trifluoroacetic acid/ 10% HPLC grade acetonitrile), in 3 minutes with a 1 minute hold at a rate of 4 mL/minute. HPLC purity was determined using a Shimadzu analytical LC at 220nm and 256nm with a Waters Sunfire C18 3.5muiotaeta 4.6 x 150mm column employing water/acetonitrile/0.1%TFA with a gradient of 10-100% B (B = 95% HPLC grade acetonitrile/ 0.1%trifluoroacetic acid/ 5% HPLC grade water), (A = 95% HPLC grade water / 0.1% trifluoroacetic acid/ 5% HPLC grade acetonitrile), inlO minutes with a 10 minute hold at a rate of 1 mL/minute. The HPLC purity was then confirmed with an orthogonal solvent system and column using a Shimadzu analytical LC with a Waters XBridge Phenyl CI 8 3.5muiotaeta 4.6 x 150mm column employing water/methanol/ lOmM ammonium bicarbonate with a gradient of 10-100% B (B = 95% HPLC grade methanol/ lOmM ammonium bicarbonate / 5% HPLC grade water), (A = 95% HPLC grade water / lOmM ammonium bicarbonate / 5% HPLC grade methanol), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. All NMR spectra were recorded at room temperature using a Bruker DRX400 spectrometer. LCMS m/z 535.16 (M+H), Rt 2.373 min. HPLC Rt 10.314 min. (Sunfire CI 8), 95.78% purity and 12.230 min. (XBridge Phenyl CI 8), 99.6 % purity. Eta NMR (400 MHz> CD3OD) delta ppm 1.40 (dd, J= 7.03, 2.01 Hz, 4 H), 3.01 (s, 3 H), 3.94 (s, 3 H), 7.18 - 7.26 (m, 2 H), 7.28 - 7.38 (m, 6 H), 7.56 - 7.62 (m, 1 H), 7.62 - 7.67 (m, 1 H), 7.85 (d, J= 1.51 Hz, 1 H), 7.94 - 8.05 (m, 4 H).

Reference： [1]Patent: WO2011/112191,2011,A1 .Location in patent: Page/Page column 303-304

12
[ 1217339-23-5 ]
[ 73930-39-9 ]
[ 1217336-97-4 ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	1 - phenylcyclopropanamine hydrochloride (16 mg, 0.091 mmol) was added to a stirring solution of HATU (43 mg, 0.1 14 mmol), DIEA (40 mu, 0.228 mmol), and 3-(2-(4- fluorophenyl)-6-(N-(2-hydroxyethyl)methylsulfonamido)-3-(methylcarbamoyl)benzofuran-5-yl)benzoic acid (40 mg, 0.076 mmol) in DMF (760 muKappa) at rt. It was allowed to stir for 1 hour. The mixture was diluted with EtOAc and washed with sat NaHC03, and sat NaCl. The organic phase was dried over Na2S04, filtered and concentrated and was purified by preparative reverse phase HPLC on a C18 column using a suitably buffered H20/CH3CN gradient, and concentrated to give the titled compound (22 mg, 44%). 1H NMR (500 MHz, DMSO-d6) d ppm 9.12 (1 H, s), 8.49 - 8.56 (1 H, m), 7.97 - 8.05 (3 H, m), 7.95 (1 H, s), 7.90 (1 H, d, J=7.93 Hz), 7.78 (1 H, d, J=7.93 Hz), 7.62 (1 H, s), 7.54 (1 H, t, J=7.78 Hz), 7.37 - 7.46 (2 H, m), 7.28 (2 H, t, J=7.63 Hz), 7.19 - 7.24 (2 H, m), 7.15 (1 H, t, J=7.32 Hz), 4.90 (1 H, t, J=5.19 Hz), 3.50 - 3.58 (1 H, m), 3.25 - 3.28 (1 H, m), 3.21 (3 H, s), 2.88 - 2.96 (2 H, m), 2.82 (3 H, d, J=4.58 Hz), 1.22 - 1.32 (4 H, m). LC-MS retention time: 1.57 min; m/z (MH+): 642. LC data was recorded on a Shimadzu LC-10AS liquidchromatograph equipped with a Waters XB ridge 5u CI 8 4.6x50mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile / 95% H20 / 10 mM ammonium acetate and solvent B was 5% H20 / 95% acetonitrile / 10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A = 5% CH3CN/95%

Reference： [1]Patent: WO2011/112191,2011,A1 .Location in patent: Page/Page column 235-236

13
[ 1332519-27-3 ]
[ 73930-39-9 ]
[ 1332518-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	2-(4-fluorophenyl)-5-(4-methoxy-2-methyl-5-(l-phenylcyclopropylcar bamoyl)phenyl)-N-methylpyrazolo[l,5-b]pyridazine-3-carboxamide. To a solution containing <strong>[73930-39-9]1-phenylcyclopropanamine hydrochloride</strong> (0.008 g, 0.05 mmol), diisopropylethylamine (0.05 mL, 0.28 mmol), 5-(2-(4-fluorophenyl)-3- (methylcarbamoyl)pyrazolo[l,5-b]pyridazin-5-yl)-2-methoxy-4-methylbenzoic acid (0.015 g, 0.04 mmol) and DMF (0.23 mL) was added HATU (0.026 g, 0.07 mmol) in one portion. The solution was maintained at room temperature for lh. The product was purified using preparative HPLC (Waters- Xbridge, 50 x 100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 0-100% B (B = 5% H20/CH3CN)/ A (A = 95% H20/ CH3CN), 15 min. gradient) to afford 2-(4-fluorophenyl)-5-(4-methoxy-2- methyl-5-(l-phenylcyclopropylcarbamoyl)phenyl)-N-methylpyrazolo[l,5- b]pyridazine-3-carboxamide as a white solid. Preparative HPLC retention time: 12.6 min. 'H NMR (400MHZ, CHLOROFORM-d) delta 8.61 (d, J=2.5 Hz, 1H), 8.43 - 8.36 (m, 2H), 8.19 (s, 1H), 7.83 - 7.72 (m, 2H), 7.35 - 7.29 (m, 4H), 7.27 - 7.15 (m, 3H), 6.97 (s, 1H), 5.65 (br. s., 1H), 4.07 (s, 3H), 2.88 (d, J=4.8 Hz, 3H), 2.45 (s, 3H), 1.40 (s, 4H). LCMS retention time: 2.230 min. LC data was recorded on a Shimadzu LC- 10AS liquid chromatograph equipped with a Phenomenex-Luna, 3 micron, CI 8, 2.0 x 50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1.0 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% methanol / 90% H20 / 10 mM TFA and solvent B was 10% H20 / 90% methanol/ 10 niM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 550 (MH+)

Reference： [1]Patent: WO2011/106340,2011,A1 .Location in patent: Page/Page column 40; 41

14
[ 1332519-05-7 ]
[ 73930-39-9 ]
[ 1332519-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 0.666667h;	4-methyl-N-( l-phenylcyclopropyl)-3-(pyridazin-4-yl)benzamide. To a solution containing 2-phenylcyclopropanamine hydrochloride (0.13 g, 0.76 mmol), diisopropylethylamine (0.88 mL, 5.0 mmol), 4-methyl-3-(pyridazin-4-yl)benzoic acid (0.14 g, 0.63 mmol) and DMF (4.2 mL) was added HATU (0.48 g, 1.3 mmol) in one portion. The solution was maintained at room temperature for 40 min. and concentrated to a residue. The residue thus obtained was purified on silica gel (0-8% methanol /dichloromethane, 45 min gradient) to afford 4-methyl-N-(l- phenylcyclopropyl)-3-(pyridazin-4-yl)benzamide. 1H NMR (500 MHz,CHLOROFORM-if) delta ppm 9.22 - 9.28 (m, 1 H), 9.18 (d, J=1.22 Hz, 1 H), 7.75 - 7.85 (m, 1 H), 7.70 (d, J=1.83 Hz, 1 H), 7.51 (dd, J=5.19, 2.44 Hz, 1 H), 7.37 - 7.42 (m, 1 H), 7.23 - 7.33 (m, 5 H), 7.15 - 7.21 (m, 2 H), 3.70 (dt, J=13.12, 6.56 Hz, 3 H), 3.17 (q, J=7.32 Hz, 3 H), 2.30 - 2.40 (m, 3 H). LCMS retention time: 1.655 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Sunfire C18, 5 micron, C18, 4.6 x 50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H20 / 10 mM TFA and solvent B was 10% H20 / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 330 (MH+)

Reference： [1]Patent: WO2011/106340,2011,A1 .Location in patent: Page/Page column 30

15
[ 1336904-76-7 ]
[ 73930-39-9 ]
[ 1336962-13-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 50℃;	3-(1 ,4'-bipiperidin-1 '-ylmethyl)-6-chloro-7-{r2-(methyloxy)ethylloxy}-//-(1-phenylcvclopropyl)- 2-[3-(trifluoromethyl)phenyll-4-quinolinecarboxamide3-(1 ,4'-Bipiperidin-1 '-ylmethyl)-6-chloro-7-[2-(methyloxy)ethyl]oxy}-2-[3- (trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.150 g, 0.247 mmol), 1- phenylcyclopropanamine hydrochloride (0.063 mg, 0.371 mmol), EDC (0.190 g, 0.990 mmol), and HOBT (0.038 g, 0.247 mmol) were combined in /V,/V-dimethylformamide (2 mL) and tetrahydrofuran (2 mL). A/JV-Diisopropylethylamine (0.432 mL, 2.475 mmol) was added and the mixture was stirred at 50C overnight. THF was removed under reduced pressure. The residue was dissolved in DMSO and purified via HPLC (Waters, 20-60% MeCN/H20 with 0.1 % TFA). The appropriate fractions were neutralized with saturated aqueousNaHC03 and extracted with methylene chloride. The combined extracts were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to give 3-(1 ,4'-bipiperidin-1 '- ylmethyl)-6-chloro-7-[2-(methyloxy)ethyl]oxy}-//-(1-phenylcyclopropyl)-2-[3- (trifluoromethyl)phenyl]-4-quinolinecarboxamide (0.090 g, 48% yield). MS (m/z) 721 .3 (M+H+).

Reference： [1]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 49

16
[ 1336905-29-3 ]
[ 73930-39-9 ]
[ 1336962-25-4 ]

Yield	Reaction Conditions	Operation in experiment
4%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In tetrahydrofuran; dichloromethane; for 18h;Reflux;	3-( 1 ,4'-bipiperidin-1 '-ylmethyl)-7-[( 1 -methylethyl)oxyl-6-(2-oxo-1 -pyrrolidinyl)-//-( 1 - phenylcvclopropyl)-2-[3-(trifluoromethyl)phenyll-4-quinolinecarboxamideA mixture of 3-(1 ,4'-bipiperidin-1 '-ylmethyl)-7-[(1 -methylethyl)oxy]-6-(2-oxo-1 - pyrrolidinyl)-2- [3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.080 g, 0.125 mmol), <strong>[73930-39-9]1-phenylcyclopropanamine hydrochloride</strong> (0.042 g, 0.250 mmol), HBTU (0.095 g, 0.250 mmol), and triethylamine (0.063 g, 0.625 mmol) in tetrahydrofuran/methylene chloride (4:1 , 2 mL) was heated to reflux for 18 h. The reaction mixture was diluted with methylene chloride, and the resulting solution was washed with saturated aqueous sodium bicarbonate (3 x 5 mL) and brine, dried over Na2S04, filtered, and concentrated in vacuo. The crude product was purified via HPLC. The appropriate fractions were neutralized with saturated aqueous NaHC03 to pH 6-7, concentrated to remove acetonitrile, and extracted with methylene chloride. The combined extracts were dried over Na2S04, filtered, and concentrated in vacuo to give 3-(1 ,4'-bipiperidin-1 '-ylmethyl)-7-r(1 -methylethyl)oxyl-6-(2-oxo-1 -pyrrolidinyl)- A/-(1-phenylcvclopropyl)-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxamide (0.004 g, 4% yield). MS (m/z) 754.3 (M+H+).

Reference： [1]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 61-62

17
[ 1383852-32-1 ]
[ 73930-39-9 ]
[ 1383852-21-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine; HATU; In N,N-dimethyl-formamide; for 4h;	In a 10 mL round-bottomed flask were combined 1 -phenylcyclopropanamine, hydrochloric acid (36.8 mg, 0.216 mmol), Example 19K (40 mg, 0.090 mmol), 0-(7-azabenzotriazol-l-yl)- A ,AyV',A etramethyluronium hexafluorophosphate (82.4 mg, 0.216 mmol) and triethylamine (0.1 mL, 0.724 mmol) in Lambda^,Lambda^-dimethylformamide (2 mL). The mixture was stirred for 4 hours, diluted with water, stirred for 5 minutes and the solid was collected by filtration. The solid was then purified by chromatography on a 12 g silica cartridge eluting with l-2%o methanol in dichloromethane to give the title compound (31 mg, 65%). .H NMR (400 MHz, DMSO-i¾) delta ppm 1.22 - 1.31 (m, 4 H) 2.34 (s, 3 H) 3.35 - 3.39 (m, 2 H) 3.82 (s, 3 H) 3.92 (t, J=4.50 Hz, 2 H) 6.94 (t, J=3.25 Hz, 1 H) 7.02 (dd, J=7.10, 1.90 Hz, 1 H) 7.04 - 7.09 (m, 2 H) 7.15 (t, J=7.16 Hz, 1 H) 7.17 - 7.31 (m, 4 H) 7.46 (d, J=7.81 Hz, 1 H) 7.57 (d, J=0.87 Hz, 1 H) 7.84 - 7.91 (m, 4 H) 8.79 (d, J=7.26 Hz, 1 H) 9.25 (s, 1 H); MS (ESI+) m/z 558 (M+H)+.

Reference： [1]Patent: WO2012/87833,2012,A1 .Location in patent: Page/Page column 162

18
[ 1383854-51-0 ]
[ 73930-39-9 ]
[ 1383854-52-1 ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 18h;	A suspension of Example 191H (84 mg, 0.15 mmol), 1 -phenylcyclopropaneamine hydrochloride (51 mg, 0.30 mmol), 0-(7-azabenzotriazol-l -yl)-A^^V,A^',A^'-tetramethyluronium hexafluorophosphate (69 mg, 0.18 mmol) in dry AyV-dimethylformamide (1.5 mL) was treated with diisopropylethylamine (132 mu,, 98 mg, 0.76 mmol) followed by stirring at room temperature for 18 hours. The mixture was diluted with ethyl acetate and extracted with water (3 x) and saturated sodium chloride solution. Drying (Na2S04), filtration, and concentration in vacuo afforded a solid, which was chromatographed over a 25 g silica gel cartridge, eluting with 5-70% acetonitrile in chloroform. These procedures afforded the title compound (62 mg, 61%) as a white rigid foam. MS (ESI+) m/z (rel abundance) 670 (100, M+H)+, 671 (44).

Reference： [1]Patent: WO2012/87833,2012,A1 .Location in patent: Page/Page column 212

19
[ 475111-38-7 ]
[ 73930-39-9 ]
[ 1401512-28-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate; for 18h;Reflux;	Example 1Synthesis of 4-(2-(difluoromethyl)-lH-benzo[<i]imidazol-l-yl)-6-morpholino-N-(l- phenylcyclopropyl)-l,3,5-triazin-2-amine Al[00248] Compound Al was prepared according to Scheme 1, where compound 1 (l-[4- chloro-6-(4-morpholinyl)-l,3,5-tianzin-2-yl]-2-(difluoromethyl)-lH-benzimidazole) was synthesized according to the procedure as described in U.S. Pat. Appl. Publ. No.2007/244110, the disclosure of which is incorporated herein by reference in its entirety.Scheme 1[00249] A mixture of compound 1 (184 mg, 0.502 mmol), <strong>[73930-39-9]1-phenylcyclopropanamine hydrochloride</strong> (170 mg, 1.00 mmol), and potassium carbonate (276 mg, 2.00 mmol) in dioxane (15 mL) was refluxed for 18 hrs. The volatiles were removed in vacuo and the residue was separated by water and ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by preparative HPLC to give 60 mg (26% yield) of compound Al as a white solid: 98.5%> purity (HPLC); MS m/z: 464.1 (M+1); 1H NMR (CDC13, 500 MHz) (rotamers) delta 8.43 and 8.13 (2d, J= 8.0 and 8.5 Hz, IH), 7.9 and 7.8 (2d, J=7.5 and 8.0 Hz, IH), 7.78-7.18 (m, 8H), 6.03 (br s, IH), 3.91-3.68 (m, 8H), 1.51-1.39 (m, 4H) ppm.

Reference： [1]Patent: WO2012/135175,2012,A1 .Location in patent: Page/Page column 94

20
[ 89793-12-4 ]
[ 73930-39-9 ]
ethyl 2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.8%		[0252] Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C. for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C. for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 85 - 95℃; for 4h;	Synthesis of Intermediate 4 Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C. for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C. for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%		Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C. for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C. for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).

86.8%		Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C. for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C. for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 85 - 95℃; for 4.3h;	Synthesis of Intermediate 4 [0270] Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C. for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C. for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 85 - 95℃; for 4h;	Synthesis of Intermediate 4: Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 mm. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C for 4 hrs. Thesolution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%		Synthesis of Intermediate 4: Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%		Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 mm. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and10 much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%		0119] Intermediate 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 mL) and stirred for 20 mL Intermediate 3 (680 g, 1.02 equiv) was added and the reaction mixture was heated to about 85-95C for 4 hrs. The solution was allowed to slowly cool to rt. This solution was poured onto H2O (20L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50C for 24 hr, yielding 896 g of intermediate 4 (solid, 86.8%).
86.8%		Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
86.8%		Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C for 24 hr., yielding 896 g of compound 4 (solid, 86.8%)
86.8%		Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 C for 24 hr., yielding 896 g of compound 4 (solid, 86.8%).
53.9%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20℃;	<strong>[73930-39-9]1-phenylcyclopropane-1-amine hydrochloride</strong> (1.000 g, 5.894 mmol), ethyl 2-chloropyrimidine-5-carboxylate (1.155 g, 6.189 mmol) and N,N-diisopropylethylamine (2.265 mL, 12.968 mmol) in 1,4-dioxane (20 mL) at room temperature was stirred at the same temperature. After removing the solvent from the reaction mixture under reduced pressure, the concentrate was crystallized from ethyl acetate (5 mL) and hexane (50 mL) at room temperature, and the resulting solid was washed with hexane and dried to give the title compound (0.900 g, 53.9 %) As a pale orange solid.

Reference： [1]Patent: US2015/99744,2015,A1 .Location in patent: Paragraph 0252
[2]Patent: US2015/105358,2015,A1 .Location in patent: Paragraph 0412
[3]Patent: US2015/105409,2015,A1 .Location in patent: Paragraph 0220
[4]Patent: US2015/105383,2015,A1 .Location in patent: Paragraph 0232
[5]Patent: US2015/150871,2015,A1 .Location in patent: Paragraph 0270
[6]Patent: WO2016/7423,2016,A1 .Location in patent: Page/Page column 42
[7]Patent: WO2016/90230,2016,A1 .Location in patent: Page/Page column 20
[8]Patent: WO2016/87950,2016,A1 .Location in patent: Page/Page column 30
[9]Patent: US2017/114023,2017,A1 .Location in patent: Paragraph 0117; 0119
[10]Patent: WO2017/143237,2017,A1 .Location in patent: Page/Page column 53; 54
[11]Patent: WO2017/184774,2017,A1 .Location in patent: Page/Page column 48; 49
[12]Patent: WO2017/214565,2017,A1 .Location in patent: Page/Page column 38; 39
[13]Patent: KR2017/43091,2017,A .Location in patent: Paragraph 0188-0191

21
[ 100-47-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of compound 1, benzonitrile, (250 g, 1.0equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to - 5 C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.OM, 2.3 equiv.) was added dropwise20 over a period of 60 mm., during which the inner temperature of the reaction was kept below 5C. The reaction mixture was allowed to warm to 15-20 C for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 mm., while the inner temperature wasmaintained below 15 C. The reaction mixture was stirred at 15-20 C for 1-2 hr. and stopped when a low level of benzonitrile remained. iN HC1 (2500 ml) was added dropwise while25 maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reactionmixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried invacuum yielding 143 g of compound 2.

Reference： [1]Patent: US2015/99744,2015,A1
[2]Patent: US2015/105409,2015,A1
[3]Patent: US2015/105383,2015,A1
[4]Patent: WO2016/87950,2016,A1 .Location in patent: Page/Page column 30

22
[ 41049-53-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
143 g	With hydrogenchloride; In tert-butyl methyl ether;	[0251] A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5 C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C. for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L×2) and EtOAc (3 L×2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45 C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g	With hydrogenchloride; In tert-butyl methyl ether;	A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5 C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C. for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L×2) and EtOAc (3 L×2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45 C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g	With hydrogenchloride; In tert-butyl methyl ether;	A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5 C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C. for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (32) and EtOAc (32), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45 C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.

Reference： [1]Patent: US2015/99744,2015,A1 .Location in patent: Paragraph 0251
[2]Patent: US2015/105409,2015,A1 .Location in patent: Paragraph 0217-0219
[3]Patent: US2015/105383,2015,A1 .Location in patent: Paragraph 0230-0231

23
[ 925-90-6 ]
[ 100-47-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
143 g		Example 4 Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) Synthesis of Intermediate 2 A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5 C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C. for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L2) and EtOAc (3 L2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45 C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g		Synthesis of Intermediate 2 A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5 C. under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C. for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C. for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L2) and EtOAc (3 L2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45 C.) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
		Synthesis of Intermediate 2: A solution of compound 1, benzonitrile, (250 g, 1.0equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to -5 C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.OM, 2.3 equiv.) was added dropwise over a period of 60 mm., during which the inner temperature of the reaction was kept below 5C. The reaction mixture was allowed to warm to 15-20 C for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 mm., while the inner temperature wasmaintained below 15 C. The reaction mixture was stirred at 15-20 C for 1-2 hr. and stopped when a low level of benzonitrile remained. iN HC1 (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, andupon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.

143 g		Synthesis of Intermediate 2: A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to - 5 C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C for 1-2 hr. and stopped when a low level of benzonitrile remained. IN HC1 (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na2S04 and concentrated under reduced pressure (below 45 C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g		0118] A solution of intermediate 1, benzonitrile, (250 g, 1.0 equiv), and Ti(OiPr)4 (1330 mL, 1.5 equiv.) in MBTE (3750 mL) was cooled to about -10 to -5C under a nitrogen atmosphere. EtMgBr (1610 mL, 3.0 M, 2.3 equiv) was added dropwise over a period of 60 min, during which the inner temperature of the reaction was kept below 5C. The reaction mixture was allowed to warm to 15-20C for 1 hr. BF3-ether (1300 mL, 2.0 equiv) was added dropwise over a period of 60 min, while the inner temperature was maintained below 15C. The reaction mixture was stirred at 15-20C for 1-2 hr and stopped when a low level of benzonitrile remained. 1N HCl (2500 mL) was added dropwise while maintaining the inner temperature below 30C. NaOH (20%, 3000 mL) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30C. The reaction mixture was extracted with MTBE (3L x 2) and EtOAc (3L x 2) and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45C) to yield a red oil. MTBE (2500 mL) was added to the oil to give a clear solution and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of intermediate 2.
		A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to - 5 C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C for 1-2 hr. and stopped when a low level of benzonitrile remained. IN HC1 (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na2S04 and concentrated under reduced pressure (below 45 C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.
143 g		A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MTBE (3750 ml) was cooled to about -10 to -5 C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C for 1-2 hr. and stopped when a low level of benzonitrile remained. 1N HCl (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure (below 45 C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HCl gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2.

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Patent: US2015/105358,2015,A1 .Location in patent: Paragraph 0411
[3]Patent: US2015/150871,2015,A1 .Location in patent: Paragraph 0269
[4]Patent: WO2016/7423,2016,A1 .Location in patent: Page/Page column 41; 42
[5]Patent: WO2016/90230,2016,A1 .Location in patent: Page/Page column 19-20
[6]Patent: US2017/114023,2017,A1 .Location in patent: Paragraph 0117; 0118
[7]Patent: WO2017/143237,2017,A1 .Location in patent: Page/Page column 53; 54
[8]Patent: WO2017/214565,2017,A1 .Location in patent: Page/Page column 38

24
[ 73930-39-9 ]
N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/7423,2016,A1
[2]Patent: WO2016/90230,2016,A1
[3]Patent: WO2016/87950,2016,A1
[4]Patent: US2017/114023,2017,A1
[5]Patent: WO2017/143237,2017,A1

25
3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-((2,2,2-trifluoroethyl)amino)furo[2,3-b]pyridin-5-yl)benzoic acid [ No CAS ]
[ 73930-39-9 ]
2-(4-fluorophenyl)-N-methyl-5-(3-((1-phenylcyclopropyl)carbamoyl)phenyl)-6-((2,2,2-trifluoroethyl)amino)furo[2,3-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]MedChemComm,2017,vol. 8,p. 796 - 806

26
[ 7647-01-0 ]
[ 6120-95-2 ]
[ 73930-39-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 549 - 554

27
[ 73930-39-9 ]
2-((1-phenylcyclopropyl)amino)pyrimidine-5-carbohydrazide [ No CAS ]

Reference： [1]Patent: KR2017/43091,2017,A

28
[ 73930-39-9 ]
N'-(2,2-difluoroacetyl)-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carbohydrazide [ No CAS ]

Reference： [1]Patent: KR2017/43091,2017,A

29
[ 73930-39-9 ]
2-((1-phenylcyclopropyl)amino)-N'-(2,2,2-trifluoroacetyl)pyrimidine-5-carbohydrazide [ No CAS ]

Reference： [1]Patent: KR2017/43091,2017,A

30
[ 73930-39-9 ]
5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)-N-(1-phenylcyclopropyl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: KR2017/43091,2017,A

31
[ 73930-39-9 ]
N-(1-phenylcyclopropyl)-5-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: KR2017/43091,2017,A

32
[ 75-16-1 ]
[ 100-47-0 ]
[ 73930-39-9 ]

Yield	Reaction Conditions	Operation in experiment
143 g		A solution of compound 1, benzonitrile, (250 g, 1.0 equiv.), and Ti(OiPr)4 (1330 ml, 1.5 equiv.) in MBTE (3750 ml) was cooled to about -10 to - 5 C under a nitrogen atmosphere. EtMgBr (1610 ml, 3.0M, 2.3 equiv.) was added dropwise over a period of 60 min., during which the inner temperature of the reaction was kept below 5 C. The reaction mixture was allowed to warm to 15-20 C for 1 hr. BF3-ether (1300 ml, 2.0 equiv.) was added dropwise over a period of 60 min., while the inner temperature was maintained below 15 C. The reaction mixture was stirred at 15-20 C for 1-2 hr. and stopped when a low level of benzonitrile remained. IN HC1 (2500 ml) was added dropwise while maintaining the inner temperature below 30 C. NaOH (20%, 3000 ml) was added dropwise to bring the pH to about 9.0, while still maintaining a temperature below 30 C. The reaction mixture was extracted with MTBE (3 L x 2) and EtOAc (3 L x 2), and the combined organic layers were dried with anhydrous Na2S04 and concentrated under reduced pressure (below 45 C) to yield a red oil. MTBE (2500 ml) was added to the oil to give a clear solution, and upon bubbling with dry HC1 gas, a solid precipitated. This solid was filtered and dried in vacuum yielding 143 g of compound 2

Reference： [1]Patent: WO2017/184774,2017,A1 .Location in patent: Page/Page column 48

33
[ 89793-12-4 ]
[ 73930-39-9 ]
N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/184774,2017,A1

34
[ 73930-39-9 ]
[ 26822-37-7 ]
[ 231961-58-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate; In ethanol; water; at 80℃; for 3h;	EXAMPLE 303 Synthesis of 3-chloro-4-((1-(1-phenylcyclopropyl)piperidin-4-yl)oxy)-//-(thiazol-4- yl)benzenesulfonamide Step 1. Preparation of 1-(1-phenylcyclopropyl)piperidin-4- To a solution of <strong>[73930-39-9]1-phenylcyclopropanamine hydrochloride</strong> (0.300 mg, 1.77 mmol) in ethanol (10 mL) was added potassium carbonate (0.0367 g, 0.265 mmol) and a mixture of 1-dimethyl-4-oxopiperidin-1-ium iodide (0.451 g, 1.77 mmol) in water (5 mL). The reaction mixture was heated to 80 C for 3 h and was then concentrated in vacuo, quenched with water (20 mL) and extracted with dichloromethane (2 chi 50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with a gradient of 0-10% of ethyl acetate in petroleum ether, to afford the title compound as an yellow solid (0.200 g, 53% yield): H NMR (400 MHz, CDCI3) 7.26- 7.36 (m, 5H), 2.82 (t, J = 6.0 Hz, 4H), 2.39 (t, J = 6.0 Hz, 4H), 1.01-1.06 (m, 2H), 0.88- 0.94 (m, 2H).

Reference： [1]Patent: WO2017/201468,2017,A1 .Location in patent: Page/Page column 402

35
[ 73930-39-9 ]
1-(1-phenylcyclopropyl)piperidin-4-ol [ No CAS ]

Reference： [1]Patent: WO2017/201468,2017,A1

36
[ 73930-39-9 ]
3-chloro-4-((1-(1-phenylcyclopropyl)piperidin-4-yl)oxy)-N-(thiazol-4-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2017/201468,2017,A1

37
[ 885280-38-6 ]
[ 73930-39-9 ]
C₂₀H₃₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 1 -phenylcyclopropanamine hydrochloride (477 mg, 2.8 mmol, 1 eq), TEA (142 mg, 1.4 mmol, 196 tL, 0.5 eq) in 10 mL ofMeOH was stirred via ultrasound equipment for 1 mm, then compound 5 (0.6 g, 2.8 mmol, 1 eq) and AcOH (84.5 mg, 1.4 mmol, 0.5 eq) was added and the mixture was stirred at 15C for 29 mins. NaBH3CN (354 mg, 5.6 mmol, 2 eq) was added and the mixture was stirred at7OC for 11.5 hours. The reaction mixture was quenched by 6 mL of H20, then concentrated under reduced pressure and extracted twice with 10 mL of EtOAc. The combined organic layers werewashed with 10 mL of brine, dried over Na2SO4, filtered and concentrated under reducedpressure to give an oil which was purified by column chromatography (Si02, eluting with agradient of petroleum ether: ethyl acetate = 5:1 to 1:1) to give 0.8 g of crude compound 80 as alight yellow oil.

Reference： [1]Patent: WO2018/119395,2018,A1 .Location in patent: Page/Page column 131

38
[ 73930-39-9 ]
C₂₂H₃₄N₂O₂ [ No CAS ]
C₂₂H₃₄N₂O₂ [ No CAS ]

Reference： [1]Patent: WO2018/119395,2018,A1

39
[ 73930-39-9 ]
C₁₇H₂₆N₂*(x)ClH [ No CAS ]

Reference： [1]Patent: WO2018/119395,2018,A1

40
[ 73930-39-9 ]
(x)C₂HF₃O₂*C₂₅H₃₀N₄O [ No CAS ]

Reference： [1]Patent: WO2018/119395,2018,A1

41
[ 73930-39-9 ]
C₂₁H₂₄⁽²⁾HNO [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

42
[ 73930-39-9 ]
C₂₀H₂₄⁽²⁾HNOSi [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

43
[ 73930-39-9 ]
N-methyl-N-(1-phenylcyclopropyl)pivalamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

44
[ 73930-39-9 ]
N-benzyl-N-(1-phenylcyclopropyl)pivalamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

45
[ 73930-39-9 ]
N,2-dimethyl-N-(1-phenylcyclopropyl)propane-2-sulfinamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

46
[ 73930-39-9 ]
N-methyl-N-(1-phenylcyclopropyl)benzamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

47
[ 73930-39-9 ]
N-methyl-N-(1-phenylcyclopropyl)-2-(trimethylsilyl)benzamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

48
[ 73930-39-9 ]
N,2-dimethyl-N-(1-phenylcyclopropyl)propane-2-sulfonamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

49
[ 73930-39-9 ]
N-methyl-N-((1RS,2SR)-2-methyl-1-phenylcyclopropyl)pivalamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

50
[ 73930-39-9 ]
N-((1RS,2SR)-2-allyl-1-phenylcyclopropyl)-N-methylpivalamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

51
[ 73930-39-9 ]
5-butyl-5-hydroxy-3,3,4,4-tetramethyl-1-(1-phenylcyclopropyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

52
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-((1RS,2SR)-2-methyl-1-phenylcyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

53
[ 73930-39-9 ]
1-((1RS,2SR)-2-allyl-1-phenylcyclopropyl)-3,3,4,4-tetramethylpyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

54
[ 73930-39-9 ]
(1SR,2RS)-2-phenyl-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)cyclopropane-1-carboxylicacid [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

55
[ 73930-39-9 ]
1-((1RS,2SR)-2-(hydroxydiphenylmethyl)-1-phenylcyclopropyl)-3,3,4,4-tetramethylpyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

56
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-((1SR,2SR)-1-phenyl-2-(phenylthio)cyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

57
[ 73930-39-9 ]
1-((1SR,2SR)-2-iodo-1-phenylcyclopropyl)-3,3,4,4-tetramethylpyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

58
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-((1SR,2SR)-1-phenyl-2-(trimethylsilyl)cyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

59
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-((1RS,2SR)-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

60
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-((1SR,2SR)-1-phenyl-2-(tributylstannyl)cyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

61
[ 73930-39-9 ]
C₁₇H₂₀⁽²⁾HNO₂ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973
[2]Organic Letters,2019,vol. 21,p. 969 - 973

62
3,3,4,4-tetramethyl-1-(methylsulfonyl)pyrrolidine-2,5-dione [ No CAS ]
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-(1-phenylcyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

63
3,3,4,4-tetramethyl-1-tosylpyrrolidine-2,5-dione [ No CAS ]
[ 73930-39-9 ]
3,3,4,4-tetramethyl-1-(1-phenylcyclopropyl)pyrrolidine-2,5-dione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

64
[ 73930-39-9 ]
[ 3282-30-2 ]
N-(1-phenylcyclopropyl)pivalamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

65
[ 73930-39-9 ]
[ 98-88-4 ]
[ 80463-28-1 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

66
[ 31562-43-3 ]
[ 73930-39-9 ]
2-methyl-N-(1-phenylcyclopropyl)propane-2-sulfinamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 969 - 973

67
1-phenylcyclopropylamine tert-butyl carbamate [ No CAS ]
[ 73930-39-9 ]

Reference： [1]ChemMedChem,2020,vol. 15,p. 643 - 658

68
[ 1214336-88-5 ]
[ 73930-39-9 ]
[ 2637453-28-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1-Methylnaphthalene at 120℃; for 18h; Inert atmosphere;	8.1 Step 1: Methyl 6-((2.3-dihydro-1H-inden-2-yl)amino-5-fluoronicotinate General procedure: To a solution of methyl 5-fluoro-6-bromonicotinate (100 mg, 0.47 mmol) in NMP (2 mL) was added 2,3-dihydro-1H-inden-2-amine (62.6 mg, 0.47 mmol) and K2CO3 (195 mg, 1.41 mmol) in a vial. The reaction mixture was stirred and heated at 120 o C under N2 for 18 h. After cooled and diluted with ethyl acetate, the organic layer was washed with water. Dried (Na2SO4), filtered and concentrated, the resulting residue was purified by chromatography (Silica gel, hexane/ethyl acetate, 1:0 to 0:1) to afford the title compound as a brown oil, 38 mg (31%). LC- MS: m/z [M+H]+ 287.3

Reference： [1]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/67859, 2021, A1 Location in patent: Paragraph 00205-00208; 00215-00218

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 73930-39-9 ] {[proInfo.proName]}

Quality Control of [ 73930-39-9 ]

Related Doc. of [ 73930-39-9 ]

Product Details of [ 73930-39-9 ]

Calculated chemistry of [ 73930-39-9 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 73930-39-9 ]

Application In Synthesis of [ 73930-39-9 ]

[ 73930-39-9 ] Synthesis Path-Upstream 1~7

[ 73930-39-9 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 73930-39-9 ]

Aryls

Amines

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Physical hazards

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[ 73930-39-9 ]