[ CAS No. 1436436-17-7 ] {[proInfo.proName]}

Name: 1436436-17-7|(R)-Morpholin-2-ylmethanol hydrochloride|95%
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Quality Control of [ 1436436-17-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1436436-17-7 ]

CAS No. :	1436436-17-7	MDL No. :	MFCD11052541
Formula :	C₅H₁₂ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NBGXGDBTUJNTKJ-NUBCRITNSA-N
M.W :	153.61	Pubchem ID :	42614735
Synonyms :

Calculated chemistry of [ 1436436-17-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	39.96
TPSA :	41.49 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.39
Log Po/w (WLOGP) :	-0.61
Log Po/w (MLOGP) :	-0.67
Log Po/w (SILICOS-IT) :	0.43
Consensus Log Po/w :	-0.25

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.48
Solubility :	50.8 mg/ml ; 0.331 mol/l
Class :	Very soluble
Log S (Ali) :	-0.02
Solubility :	147.0 mg/ml ; 0.96 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.33
Solubility :	72.3 mg/ml ; 0.471 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.2

Safety of [ 1436436-17-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1436436-17-7 ]

* 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.

Downstream synthetic route of [ 1436436-17-7 ]

[ 1436436-17-7 ] Synthesis Path-Downstream 1~17

1
[ 1436436-17-7 ]
[ 1643499-67-5 ]
[ 1643500-17-7 ]

Yield	Reaction Conditions	Operation in experiment
21%	With copper(l) iodide; potassium carbonate; <i>L</i>-proline In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	75.1 Step 1 : (R -(4-(6-Chloro-l-isopropyl-lH-pyrazolor4 -c1pyridin-3-yl mo^holin-2-yl methanol A mixture of 6-chloro-3-iodo-l-isopropyl-lH-pyrazolo[4,3-c]pyridine (500 mg, 1.55 mmol)(Example 1, step 8), (R)-morpholin-2-ylmethanol hydrochloride (950 mg, 6.18 mmol), copper(I) iodide (30.0 mg, 0.160 mmol), (S)-pyrrolidine-2-carboxylic acid (37.0 mg, 0.320 mmol) and potassium carbonate (1.32 g, 9.55 mmol) in NN-dimethylformamide (10 mL) was stirred overnight at 80 °C under nitrogen atmosphere. The solution was diluted with water (20 mL). The resulting solution was extracted with dichloromethane (3x), washed with brine, dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (solvent gradient: 0-50% ethyl acetate in petroleum) to afford the title compound (100 mg, 21%) as a white solid. LCMS (ESI): [M+H]+ = 311.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2014/210354, 2014, A1 Location in patent: Page/Page column 128

2
(R)-morpholin-2-ylmethanol hydrochloric acid salt [ No CAS ]
[ 507476-70-2 ]
(R)-5-(2-(hydroxymethyl)morpholino)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46.9%	In 1-methyl-pyrrolidin-2-one; at 170℃; for 16h;	A mixture of Compound 3 (201 mg, 0.862 mmol) and (R)-2-hydroxymethyl morpholine hydrochloride (132, 0.856 mmol) in NMP(3 mL) was heated to 170 C. for 16 h. The completed reaction was cooled, filtered, eluted with MeOH (2 mL) then purified directly by HPLC using a C-18 column eluting with a 10-100% acetonitrile in water containing 0.1% TFA. The desired product was collected and concentrated to dry. The resulting product was dissolved in MeOH (2 mL) and passed over a basic silica plug (Biotage, 1 g, SiCO3) eluting with MeOH (5 mL) to provide (R)-5-(2-(hydroxymethyl)morpholino)quinoline-8-carbonitrile or ER-886849 (108 mg, 0.401 mmol, 46.9% yield).

Reference： [1]Patent: US2015/105370,2015,A1 .Location in patent: Paragraph 0334

3
[ 1195-34-2 ]
[ 1436436-17-7 ]
[ 2072807-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In isopropyl alcohol at 90℃; for 1h;	D418 Description D41 8(R)-(4-(6-Chloro-2-ethylpyrimidin-4-yl)morpholin-2-yl)methanol (D41 8) To a solution of 4,6-dichloro-2-ethylpyrimidine (84 mg, 0.46 mmol) in i-PrOH (8 mL) wasadded (R)-morpholmn-2-ylmethanol hydrochloride (123 mg, 0.691 mmol) and TEA (209 mg, 1.38 mmol). The resulting mixture was stirred at 90 °C for 1 h. The mixture was concentratedand purified by column (PE: EtOAc from 5: ito 1: 1)to give the title compound (139 mg,yield >100%) as a slight yellow solid.D418 1H NMR (300 MHz, CDCI3): 6634 (s, IH), 4.26-4.03 (m, 3H), 3.80-3.61 (m, 4H), 3.13-3.03 (m, 1 H), 2.96-2.89 (m, 1 H), 2.75 (q, J = 7.5 Hz, 2H), 2.05-1.94 (m, 1 H), 1.28 (t, J = 7.5Hz, 3H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/12576, 2017, A1 Location in patent: Page/Page column 277

4
[ 1436436-17-7 ]
[ 164738-58-3 ]
[ 2072806-94-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 2h;
	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol	A-15 (R)-(4-(6-Iodo-2-methoxypyrimidin-4-yl)morpholin-2-yl)methanol (D A-15): The title compound was prepared by a procedure similar to those described for D A-3 starting from a solution of 4, 6-diiodo-2-methoxypyrimidine and (R) -morpholin-2-ylmethanol hydrochloride in iPrOH and DIPEA. LC-MS [mobile phase: from 50%water (0.1%FA) and 50%CH3CN (0.1%FA) to 5%water (0.1%FA) and 95%CH3CN (0.1%FA) in 2.6 min] : Rt = 0.92 min; MS Calcd: 351.1, MS Found: 352.0 [M + H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137573, 2018, A1 Location in patent: Page/Page column 45; 55
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137619, 2018, A1 Location in patent: Page/Page column 52; 57

5
[ 1436436-17-7 ]
[ 66298-49-5 ]
[ 2072806-84-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In methanol at 70℃; for 2h;
639 mg	With triethylamine In methanol at 70℃; for 2h;	116 Description 116 (R) - (4- (6-Iodo-2-methylpyrimidin-4-yl) morpholin-2-yl) methanol (D116) To a solution of (R) -morpholin-2-ylmethanol hydrochloride (423 mg crude, 2.30 mmol) in CH3OH (10 mL) was added 4, 6-diiodo-2-methylpyrimidine (954 mg, 2.75 mmol) and TEA (835 mg, 8.25 mmol) . The resulting mixture was warmed to 70 and stirred for 2 hrs. LCMS showed that the reaction was completed. The reaction mixture was concentrated to remove solvent, poured into water (40 mL) and extracted with EtOAc (40 mL x 2) . The combined organic layers were washed with brine, dried over Na2SO4and concentrated. The residue was purified by column (PEEA = 21) to give the title compound (639 mg, yield 83%) as a white solid. 1H NMR (300 MHz, CDCl3) : δ 6.79 (s, 1H) , 4.22-4.01 (m, 3H) , 3.79-3.56 (m, 4H) , 3.08-2.98 (m, 1H) , 2.88-2.84 (m, 1H) , 2.46 (s, 3H) , 2.09-2.04 (m, 1H) .
639 mg	With triethylamine In methanol at 70℃; for 2h;	A-13 (R)-(4-(6-Iodo-2-methylpyrimidin-4-yl)morpholin-2-yl)methanol (D A-13) To a solution of (R)-morpholin-2-ylmethanol hydrochloride (423 mg crude, 2.30 mmol) in CH3OH (10 mL) was added 4,6-diiodo-2-methylpyrimidine (954 mg, 2.75 mmol) and TEA (835 mg, 8.25 mmol). The resulting mixture was warmed to 70 and stirred for 2 hrs. LCMS showed that the reaction was completed. The reaction mixture was concentrated to remove solvent, poured into water (40 mL) and extracted with EtOAc (40 mL × 2) . The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column (PEEA = 21) to give the title compound (639 mg, yield 83%) as a white solid. 1H NMR (300 MHz, CDCl3) : δ 6.79 (s, 1H) , 4.22-4.01 (m, 3H) , 3.79-3.56 (m, 4H) , 3.08-2.98 (m, 1H) , 2.88-2.84 (m, 1H) , 2.46 (s, 3H) , 2.09-2.04 (m, 1H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137573, 2018, A1 Location in patent: Page/Page column 50
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137607, 2018, A1 Location in patent: Page/Page column 88-89
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137619, 2018, A1 Location in patent: Page/Page column 56

6
[ 135065-71-3 ]
(R)-morpholin-2-ylmethanol hydrochloric acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1h;	To a solution of (R) -tert-butyl 2- (hydroxymethyl) morpholine-4-carboxylate (500 mg, 2.30 mmol) was added HCl/dioxane (4 M, 10 mL) and stirred for 1 h at rt. TLC showed that the reaction was completed. The reaction was concentrated to give the title compound (420 mg, yield100%) as a white solid. 1H NMR (300 MHz, DMSO-d6) : delta 9.67 (s, 1H) , 9.38 (s, 1H) , 3.94-3.88 (m, 1H) , 3.77-3.67 (m, 2H) , 3.45-3.33 (m, 2H) , 3.13 (t, J = 12.6 Hz, 2H) , 2.95-2.87 (m, 1H) , 2.78-2.67 (m, 1H) .
	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1h;	To a solution of (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (500 mg, 2.30 mmol) was added HCl/dioxane (4 M, 10 mL) and stirred for 1 h at rt. TLC showed that the reaction was completed. The reaction was concentrated to give the title compound (420 mg, yield 100%) as a white solid. 1H NMR (300 MHz, DMSO-d6) : delta 9.67 (s, 1H) , 9.38 (s, 1H) , 3.94-3.88 (m, 1H) , 3.77-3.67 (m, 2H) , 3.45-3.33 (m, 2H) , 3.13 (t, J = 12.6 Hz, 2H) , 2.95-2.87 (m, 1H) , 2.78-2.67 (m, 1H).

Reference： [1]Patent: WO2018/137573,2018,A1 .Location in patent: Page/Page column 50
[2]Patent: WO2018/137607,2018,A1 .Location in patent: Page/Page column 88
[3]Patent: WO2018/137619,2018,A1 .Location in patent: Page/Page column 56

7
[ 1436436-17-7 ]
[ 66298-49-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20 - 70℃; for 48h;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137573, 2018, A1 Location in patent: Page/Page column 89

8
[ 1436436-17-7 ]
[ 2241402-79-7 ]
[ 2241402-80-0 ]

Yield	Reaction Conditions	Operation in experiment
110 mg	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃;	84 Description 84 (R) -1- (4- (5-chloro-1- (6- (2- (hydroxymethyl) morpholino) -2-methylpyrimidin-4-yl) -1H-indazol-6-yl) piperidin-1-yl) propan-2-one (D84) To a solution of 1- (4- (5-chloro-1- (6-chloro-2-methylpyrimidin-4-yl) -1H-indazol-6-yl) piperidin-1-yl) propan-2-one (120 mg, 0.290 mmol) and (R) -morpholin-2-ylmethanol hydrochloride (D114, 44.0 mg, 0.290 mmol) in DMF (30.0 mL) was added DIEA (187 mg, 1.45 mmol) at rt. The reaction mixture was stirred at 80 overnight, cooled to room temperature, diluted with water (50 mL) and extracted with EtOAc (50 mL x 3) . The combined organic layers were washed with water (50 mL x 3) and brine (50 mL) , dried, filtered and concentrated to give the title product as a yellow solid (110 mg, yield: 76.0%) . LC-MS [mobile phase: from 50%water (0.1%TFA) and 50%CH3CN (0.1%TFA) to 5%water (0.1%TFA) and 95%CH3CN (0.1%TFA) in 2.6 min] : Rt = 0.78 min; MS Calcd.: 498.2, MS Found: 499.2 [M + H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137607, 2018, A1 Location in patent: Page/Page column 73-74

9
[ 1436436-17-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
79 mg	With triethylamine In 1-methyl-pyrrolidin-2-one at 60℃; for 2h;	90 Description 90 1- (cis-3-fluoro-4- (1- (6- ( (R) -2- (hydroxymethyl) morpholino) -2-methylpyrimidin-4-yl) -5-methyl-1H-indazol-6-yl) piperidin-1-yl) propan-2-one (D90) A solution of 1- (cis-4- (1- (6-chloro-2-methylpyrimidin-4-yl) -5-methyl-1H-indazol-6-yl) -3-fluoropiperidin-1-yl) propan-2-one (D89,. 70.7 mg, 0.170 mmol) , (R) -morpholin-2-ylmeth-anol hydrochloride (D116, 153 mg, 1.00 mmol) and Et3N (1 mL) in NMP (10 mL) was stirred at 60 for 2h, diluted with EtOAc (50 mL) , washed with brine (50 mL x 3) . The organic solution was dried and concentrated. The residue was purified by prep-TLC (MeOH/DCM=1/10) to give the title product as a white solid (79.0 mg, 99.0%yield) LC-MS [mobile phase: from 80%water (0.1%TFA) and 20%CH3CN (0.1%TFA) to 5%water (0.1%TFA) and 95%CH3CN (0.1%TFA) in 2.0 min] : Rt = 1.09 min; MS Calcd.: 496.3, MS Found: 497.3 [M + H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137607, 2018, A1 Location in patent: Page/Page column 76-77

10
[ 1628627-36-0 ]
[ 1436436-17-7 ]
[ 2280989-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 70 - 80℃;	83.83A (R)-(4-(4-(((tert-butyldimethylsilyl)oxy)methyl)pyrimidin-2-yl)morpholin-2-yl)methanol To a mixture of Example 38A (310 mg) and (R)-morpholin-2-ylmethanol, hydrochloric acid salt (290 mg) in dioxane (5 mL) was added NN-diisopropylethylamine (830 μ), and the mixture was heated at 90 °C for 5 hours and at 70 °C overnight. The reaction was then heated at 85 °C for 6 hours and concentrated. The reaction was diluted with ethyl acetate and water, and the layers were separated. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using an 80 g cartridge to give the title compound. NMR (400 MHz, CDC13) δ ppm 8.32 (d, 1H), 6.77 (d, 1H), 4.59 (s, 2H), 4.55-4.43 (m, 2H), 4.09-3.96 (m, 1H), 3.82-3.56 (m, 4H), 3.14-3.00 (m, 1H), 2.94-2.79 (m, 1H), 1.99 (br s, 1H), 0.95 (s, 9H), 0.11 (s, 6H).

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/35927, 2019, A1 Location in patent: Paragraph 00629

11
[ 1436436-17-7 ]
[ 501-53-1 ]
[ 500702-97-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; acetonitrile	1 Step 1-Benzyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate To a solution of [(2R)-morpholin-2-yl]methanol (2.50 g, 16.2 mmol, HCl, CAS156925-22-3), NaHCO3 (4.10 g, 48.8 mmol) in a mixed solvent of ACN (80.0 mL) and H2O (80.0 mL) was added CbzCl (4.16 g, 24.4 mmol, 3.47 mL) at 0° C. dropwise. The mixture was then stirred at 25° C. for 16 hrs. On completion, the mixture was concentrated in vacuo to remove ACN. Then the mixture was extracted with EA (2×20 mL), and the combined organic layers were concentrated in vacuo. The residue was purified by silica gel column (PE:EA=1:1) to give the title compound (3.7 g, 90% yield) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.42-7.33 (m, 5H), 5.17 (d, J=2.0 Hz, 2H), 4.08-3.88 (m, 3H), 3.77-3.65 (m, 1H), 3.63-3.46 (m, 3H), 3.13-2.73 (m, 2H), 2.07-1.96 (m, 1H).
90%	With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; acetonitrile at 0 - 25℃; for 16h; Inert atmosphere;	1 Step 1 - Benzyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate To a solution of [(2R)-morpholin-2-yl]methanol (2.50 g, 16.2 mmol, HCl, CAS 156925-22-3), NaHCO3 (4.10 g, 48.8 mmol) in a mixed solvent of ACN (80.0 mL) and H2O (80.0 mL) was added CbzCl (4.16 g, 24.4 mmol, 3.47 mL) at 0 °C dropwise. The mixture was then stirred at 25 °C for 16 hrs. On completion, the mixture was concentrated in vacuo to remove ACN. Then the mixture was extracted with EA (2 X 20 mL), and the combined organic layers were concentrated in vacuo. The residue was purified by silica gel column (PE: EA=1: 1) to give the title compound (3.7 g, 90% yield) as colorless oil.1H NMR (400MHz, CDCl3) d 7.42 - 7.33 (m, 5H), 5.17 (d, J = 2.0 Hz, 2H), 4.08 - 3.88 (m, 3H), 3.77 - 3.65 (m, 1H), 3.63 - 3.46 (m, 3H), 3.13 - 2.73 (m, 2H), 2.07 - 1.96 (m, 1H).
90%	With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; acetonitrile at 0 - 25℃; for 16h;	1 Step 1 - Benzyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate To a solution of [(2R)-morpholin-2-yl]methanol (2.50 g, 16.2 mmol, HCl, CASNo. 156925- 22-3), NaHCO3 (4.10 g, 48.8 mmol) in a mixed solvent of ACN (80.0 mL) and H2O (80.0 mL) was added CbzCl (4.16 g, 24.4 mmol, 3.47 mL) at 0 °C dropwise. The mixture was then stirred at 25 °C for 16 hrs. On completion, the mixture was concentrated in vacuo to remove ACN. Then the mixture was extracted with EA (2 X 20 mL), and the combined organic layers were concentrated in vacuo. The residue was purified by silica gel column (PE: EA=1: 1) to give the title compound (3.7 g, 90% yield) as colorless oil. 1H NMR (400MHz, CDCl3) δ 7.42 - 7.33 (m, 5H), 5.17 (d, J = 2.0 Hz, 2H), 4.08 - 3.88 (m, 3H), 3.77 - 3.65 (m, 1H), 3.63 - 3.46 (m, 3H), 3.13 - 2.73 (m, 2H), 2.07 - 1.96 (m, 1H).

90%	With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; acetonitrile at 0 - 25℃; for 16h;	1 Step 1 - Benzyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate To a solution of [(2R)-morpholin-2-yl]methanol (2.50 g, 16.2 mmol, HCl, CASNo. 156925- 22-3), NaHCO3 (4.10 g, 48.8 mmol) in a mixed solvent of ACN (80.0 mL) and H2O (80.0 mL) was added CbzCl (4.16 g, 24.4 mmol, 3.47 mL) at 0 °C dropwise. The mixture was then stirred at 25 °C for 16 hrs. On completion, the mixture was concentrated in vacuo to remove ACN. Then the mixture was extracted with EA (2 X 20 mL), and the combined organic layers were concentrated in vacuo. The residue was purified by silica gel column (PE: EA=1: 1) to give the title compound (3.7 g, 90% yield) as colorless oil. 1H NMR (400MHz, CDCl3) δ 7.42 - 7.33 (m, 5H), 5.17 (d, J = 2.0 Hz, 2H), 4.08 - 3.88 (m, 3H), 3.77 - 3.65 (m, 1H), 3.63 - 3.46 (m, 3H), 3.13 - 2.73 (m, 2H), 2.07 - 1.96 (m, 1H).
61.1%	With Sodium hydrogenocarbonate In tetrahydrofuran; lithium hydroxide monohydrate at 20 - 25℃;	24.1 Step 1: (R)-benzyl 2-(hydroxymethyl)morpholine-4-carboxylate To a stirred mixture of (R)-morpholin-2-ylmethanol hydrochloride (2.0 g, 13.02 mmol, 1.00 eq.) and NaHCCh (2.2 g, 26.19 mmol, 2.01 eq.) in THF/H2O = 1/1 (40 mL) was added benzyl chloroformate (2.9 g, 17.00 mmol, 1.31 eq.) at RT. After stirring at 25 °C overnight, the reaction mixture was diluted with water and then extracted with EtOAc The organic layer was washed with brine, dried as purified by chromatograph on silica gel (PE/EA = 1/1) to give the title compound (2.0 g, 61.1%) as a colorless oil.

Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - US2019/192668, 2019, A1 Location in patent: Paragraph 4116; 4117
[2]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1 Location in patent: Paragraph 00962; 001684-001686
[3]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2021/188948, 2021, A1 Location in patent: Paragraph 001200; 001201-001202
[4]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2021/188948, 2021, A1 Location in patent: Paragraph 001200; 001201-001202
[5]Current Patent Assignee: NIKANG THERAPEUTICS INC - WO2022/140472, 2022, A1 Location in patent: Page/Page column 178-179

12
[ 1436436-17-7 ]
[ 2414509-56-9 ]
[ 2414509-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; for 2h;	9.4; 12.4 Step 4: Into a lOO-mL 3-necked round-bottom flask, was placed (2R)-morpholin-2-ylmethanol hydrochloride (0.70 g, 4.56 mmol, 1.00 equiv), DCM (20.00 mL), and Et3N (1.84 g, 18.23 mmol, 4.00 equiv). This was followed by the addition of 3-ethoxy-2-formylbenzoyl chloride (1.07 g, 5.03 mmol, 1.10 equiv), in portions at 0 ?C. The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 3 x 20 mL of dichloromethane, and the organic layers were combined and dried over anhydrous sodium sulfate and concentrated. The residue was applied onto a silica gel column with THF/PE (50%). This resulted in 2-ethoxy-6-[(2R)-2-(hydroxymethyl)morpholine-4-carbonyl]benzaldehyde.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/72377, 2020, A1 Location in patent: Paragraph 0271; 0293

13
[ 1436436-17-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h;	5 Example 5.2-((3bR,4aR)-3-((R)-2-(hydroxymethyl)morpholine-4-carbonyl)-3b,4,4a,5- tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-1-(4-(2-methyl-3- (trifluoromethyl)phenyl) piperidin-1-yl)ethanone To a stirred solution of (3bR,4aR)-1-(2-(4-(2-methyl-3- (trifluoromethyl)phenyl)piperidin-1-yl)-2-oxoethyl)-3b,4,4a,5-tetrahydro-1H- cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-3-carboxylic acid (20 mg, 0.045 mmol) in DCM (3 mL) were added HATU (26 mg, 0.068 mmol), DIEA (0.03 mL, 0.172 mmol) and followed by (R)-morpholin-2-ylmethanol hydrochloride (8 mg, 0.052 mmol) at RT. After the addition was complete, the mixture was stirred at RT. The reaction was monitored by LCMS. After stirring at RT for 1 h, the reaction was finished to afford a solution. After concentration in vacuo, the residue was purified by reversed phase HPLC on a GILSON 281 instrument fitted with a Phenomenex Synergi C18150x30mmx4um column using water (0.1% TFA)-ACN as eluents (Mobile phase A water (0.1% TFA), Mobile phase B ACN, Detective wavelength 220 nm) and concentration to give the title compound as a solid. 1H NMR (400 MHz, CD3OD) d 7.43 - 7.54 (m, 2 H), 7.28 - 7.36 (m, 1 H), 4.95 - 5.17 (m, 2 H), 4.41 - 4.67 (m, 3 H), 3.86 - 4.12 (m, 2 H), 3.48 - 3.67 (m, 4 H), 3.33 (br d, J=4.4 Hz, 1 H), 3.20 - 3.27 (m, 1 H), 2.72 - 3.29 (m, 5 H), 2.48 (s, 3 H), 2.15 (br s, 2 H), 1.82 (br d, J=8.4 Hz, 2 H), 1.55 - 1.77 (m, 2 H), 1.07 - 1.19 (m, 1 H), 0.28 - 0.36 (m, 1 H); MS (ESI) m/z: 547.3[M+H+].

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2020/92183, 2020, A1 Location in patent: Page/Page column 37

14
[ 28920-43-6 ]
[ 1436436-17-7 ]
[ 2746380-99-2 ]

Yield	Reaction Conditions	Operation in experiment
96.99%	With sodium carbonate In 1,4-dioxane; water at 0 - 10℃; for 12h;	20 To a solution of Fmoc-Cl (47.16 g, 182.28 mmol) in dioxane (600 mL) was added Na2CO3 (57.96 g, 546.85 mmol) in H2O (500 mL), followed by compound 1R (28 g, 182.28 mmol) in dioxane (600 mL) added dropwise at 0-5 °C, then the mixture was stirred at 5 - 10 °C for 12 hrs. LCMS showed desired MS was detected. TLC showed the reaction was completed, staring material was consumed. The mixture was diluted with H2O (500 mL) and extracted with EtOAc (500 mL*4), the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=1/0 to 0/1). Compound 2R (60 g, 96.99% yield) was obtained as a white oil. LCMS: M+H+ = 340.1. TLC (Petroleum ether : Ethyl acetate = 0:1 ) Rf= 0.32.

Reference： [1]Current Patent Assignee: WAVE LIFE SCIENCES LTD. - WO2021/237223, 2021, A1 Location in patent: Paragraph 00679-00680

15
[ 1436436-17-7 ]
[ 2841394-55-4 ]
[ 2841394-56-5 ]

Yield	Reaction Conditions	Operation in experiment
76 %	With N-ethyl-N,N-diisopropylamine In butan-1-ol Reflux;	3.2 The second step: Synthesis of Compound (R)-3-((4-phenoxymethyl)phenyl)-4-(3-3-hydroxymethylpiperidin-1-yl)-1-(2-(trimethylsilyl)ethoxymethyl)-4-chloropyrrolo[2,3-d]pyrimidine 3b (R)-morpholine-2-methanol hydrochloride (431 mg, 2.81 mmol) and N,N-diisopropylethylamine (1.23 g, 10.2 mmol) were added to 4-chloro-5-(4-(phenoxymethyl)phenyl)-7-(2-(trimethylsilyl)ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (1.23g, 2.56mmol) in n-butyl alcohol (30 mL), and the reaction mixture was heated at reflux for 18 hours, then concentrated under reduced pressure. Aqueous hydrochloric acid (0.1M, 100 mL) was added and the resulting solid was collected by filtration, washed with water (20 mL) and dried under vacuum to afford the product (R)-3-(4-(pyridin-2-aminoacyl) as a yellow solid Phenyl)-4-(3-3-hydroxymethylpiperidin-1-yl)-1-(2-(trimethylsilyl)ethoxymethyl)-4-chloropyrrolo[2,3 -d] Pyrimidine (1.06 g, 76%).

Reference： [1]Current Patent Assignee: YAOYA TECH SHANGHAI - CN115073469, 2022, A Location in patent: Paragraph 0104-0105; 0108-0109

16
[ 1207543-30-3 ]
[ 1436436-17-7 ]
[ 2841394-53-2 ]

Yield	Reaction Conditions	Operation in experiment
62 %	With N-ethyl-N,N-diisopropylamine In butan-1-ol Reflux;	1.2 The second step: Synthesis of (R)-4-(3-3-hydroxymethylpiperidin-1-yl)-1-(2-(trimethylsilyl)ethoxymethyl)-3-iodopyrrolo [2,3-d]pyrimidine 1c (R)-Morpholine-2-methanol hydrochloride (4.31 g, 28.1 mmol) and N, N-diisopropylethylamine (12.3 g, 100.2 mmol) were added to 7-(2-(trimethylsilyl)ethoxymethyl)-4-chloro-5-iodopyrrolo[2,3-d]pyrimidine (12.3 g, 25.6 mmol) was dissolved in n-butanol (300 mL) and the reaction mixture was heated at reflux for 18 hours, Then concentrated under reduced pressure. Aqueous hydrochloric acid (0.1M, 1000 mL) was added and the resulting solid was collected by filtration, washed with water (20 mL) and dried under vacuum to afford the product (R)-4-(3-3-hydroxymethylpiperidine- 1-yl)-1-(2-(trimethylsilyl)ethoxymethyl)-3-iodopyrrolo[2,3-d]pyrimidine (7.78 g, 62%).

Reference： [1]Current Patent Assignee: YAOYA TECH SHANGHAI - CN115073469, 2022, A Location in patent: Paragraph 0091-0092; 0095-0096

17
[ 1436436-17-7 ]
[ 2857047-90-4 ]
[ 2857046-43-4 ]

Yield	Reaction Conditions	Operation in experiment
32 mg	Stage #1: (R)-morpholin-2-ylmethanol hydrochloride; 2-[2-[[3-(2-amino-6-chloro-pyrimidin-4-yl)-1-(difluoro methyl)pyrazol-4-yl]methyl]phenoxy]acetaldehyde With acetic acid at 20℃; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; Inert atmosphere;

Reference： [1]Miller, Michael; Rossetti, Thomas; Ferreira, Jacob; Ghanem, Lubna; Balbach, Melanie; Kaur, Navpreet; Levin, Lonny R.; Buck, Jochen; Kehr, Maria; Coquille, Sandrine; Van Den Heuvel, Joop; Steegborn, Clemens; Fushimi, Makoto; Finkin-Groner, Efrat; Myers, Robert W.; Kargman, Stacia; Liverton, Nigel J.; Huggins, David J.; Meinke, Peter T. [Journal of Medicinal Chemistry, 2022, vol. 65, # 22, p. 15208 - 15226]

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[ 1436436-17-7 ] Synthesis Path-Downstream 1~17

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Alcohols

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Aliphatic Heterocycles

Morpholines

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