[ CAS No. 193274-53-2 ] {[proInfo.proName]}

Name: 193274-53-2|Methyl 1-Boc-3-methyl-4-oxo-piperidine-3-carboxylate|95%
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SKU: A181808
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2D 3D

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Quality Control of [ 193274-53-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 193274-53-2 ]

Product Details of [ 193274-53-2 ]

CAS No. :	193274-53-2	MDL No. :	MFCD11506200
Formula :	C₁₃H₂₁NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IDSNQTJSDFUAEV-UHFFFAOYSA-N
M.W :	271.31	Pubchem ID :	66758517
Synonyms :

Calculated chemistry of [ 193274-53-2 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.77
Num. rotatable bonds :	5
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.24
TPSA :	72.91 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) :	-7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.82
Log Po/w (XLOGP3) :	1.05
Log Po/w (WLOGP) :	0.99
Log Po/w (MLOGP) :	0.67
Log Po/w (SILICOS-IT) :	1.26
Consensus Log Po/w :	1.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.85
Solubility :	3.8 mg/ml ; 0.014 mol/l
Class :	Very soluble
Log S (Ali) :	-2.17
Solubility :	1.83 mg/ml ; 0.00673 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.85
Solubility :	3.87 mg/ml ; 0.0143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.99

Safety of [ 193274-53-2 ]

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 [ 193274-53-2 ]

* 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 [ 193274-53-2 ]

[ 193274-53-2 ] Synthesis Path-Downstream 1~25

Yield	Reaction Conditions	Operation in experiment
		17.A A. A. 3Methyl-4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-(R,S)-methyl ester To a solution of 2.00 g (7.77 mmol) 3A in 30 mL of DMF was added 308 mg (7.77 mmol) of sodium hydride (60% oil dispersion) and the mixture was stirred at room temperature for about 25 min. To the stirring solution was added 0.50 mL (7.77 mmol) of methyl iodide and the mixture was stirred for about 17 h at room temperature. The mixture was diluted with ethyl acetate and washed once with water and four times with brine, dried over MgSO4, and concentrated. The residue was purified by silica gel chromatography (7:3 v/v hexane:ethyl acetate) to give 1.75 g of 17A as a clear oil. MS (Cl, NH3) 272 (MH+).
		17.A A. A. 3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-(R,S)-methyl ester To a solution of 2.00 g (7.77 mmol) 3A in 30 mL of DMF was added 308 mg (7.77 mmol) of sodium hydride (60% oil dispension) and the mixture was stirred at room temperature for about 25 min. To the stirring solution was added 0.50 mL (7.77 mmol) of methyl iodide and the mixture was stirred for about 17 h at room temperature. The mixture was diluted with ethyl acetate and washed once with water and four times with brine, dried over MgSO4, and concentrated. The residue was purified by silica gel chromatography (7:3 v/v hexane:ethyl acetate) to give 1.75 g of 17A as a clear oil. MS (Cl, NH3) 272 (MH+).

2
[ 161491-24-3 ]
[ 74-88-4 ]
[ 193274-53-2 ]

Yield	Reaction Conditions	Operation in experiment
80.1%	With potassium carbonate In acetone at 20 - 40℃; for 6h; Inert atmosphere;
52%	With NaH In tetrahydrofuran; hexane; ethyl acetate	481.2 Step 2: Step 2: 3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl Ester 3-methyl Ester 4-Oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2.00 g, 6.8 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added NaH (0.300 g, 12.5 mmol) portionwise over 1 h. H2(g) was evolved during the addition. The reaction was allowed to stir for 30 minutes at 0° C. and then methyl iodide (0.422 mL, 6.8 mmol) was added and allowed to stir at room temperature for 13 h. The reaction was quenched with ice water and concentrated down. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with EtOAc (3*), the organics were collected together dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (10% ethyl acetate/90% hexane to yield the title compound (1.1 g, 52%). 1H-NMR (CDCl3): δ 1.29 (s, 3H), 1.47 (s, 9H), 2.47 (dt, 1H), 2.76 (m, 1H), 3.07 (d, 1H), 3.33 (dt, 1H), 3.71 (s, 3H), 4.11 (m, 1H), 4.50 (d, 1H).
52%	Stage #1: methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 13.5h;	481.2 3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl ester 3-methyl ester Step 2 3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl ester 3-methyl ester 4-Oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2.00 g, 6.8 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added NaH (0.300 g, 12.5 mmol) portionwise over 1 h. H2(g) was evolved during the addition. The reaction was allowed to stir for 30 minutes at 0° C. and then methyl iodide (0.422 mL, 6.8 mmol) was added and allowed to stir at room temperature for 13 h. The reaction was quenched with ice water and concentrated down. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with EtOAc (3*), the organics were collected together dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (10% ethyl acetate/90% hexane to yield the title compound (1.1 g, 52%). 1H-NMR (CDCl3): δ 1.29 (s, 3H), 1.47 (s, 9H), 2.47 (dt, 1H), 2.76 (m, 1H), 3.07 (d, 1H), 3.33 (dt, 1H), 3.71 (s, 3H), 4.11 (m, 1H), 4.50 (d, 1H).

	Stage #1: methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 44h;	2 A solution of O1-tert-butyl O3-methyl 4-oxopiperidine-1,3-dicarboxylate (1 g, 3.88 mmol) in DMF (100 mL) was cooled to 0° C. followed by portion wise addition of NaH (60% dispersion of mineral oil, 0.16 g, 3.88 mmol). The resulting mixture was stirred at the same temperature for 15 min followed by addition of MeI (0.7 mL, 11.64 mmol) at 0° C. then stirred at rt for 44 h. After completion of reaction (by TLC), water (100 mL) was added and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the product as a yellow oil (0.9 g). MS: 272.12 [M+H]+.
	With potassium carbonate In acetone for 7h; Reflux;	5.01 a: 3-Methyl-4-oxo-piperidine-1 ,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester A mixture of 4-oxo-piperidine-1 ,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1 g, 4 mmol), potassium carbonate (1.1 g, 8 mmol) and iodomethane (1.13 g, 8 mmol) in acetone (12 mL) is heated under reflux for 7 h. The mixture is then cooled to RT and filtered through a fritted filter. The filtrate is concentrated under reduced pressure to yield the title compound as a yellowish oil. LC-MS method A: tR = 0.78 min; [M+H]+ = 272.21.

Reference： [1]Location in patent: experimental part Chai, Yun; Wan, Zhi-Long; Wang, Bo; Guo, Hui-Yuan; Liu, Ming-Liang [European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4063 - 4069]
[2]Current Patent Assignee: KIRIN HOLDINGS CO LTD; TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2005/70549, 2005, A1
[3]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1 Location in patent: Paragraph 1393
[4]Current Patent Assignee: SPERO THERAPEUTICS INC - US2012/88750, 2012, A1 Location in patent: Page/Page column 28; 29
[5]Current Patent Assignee: JOHNSON & JOHNSON INC; IDORSIA PHARMACEUTICALS LTD - WO2018/19929, 2018, A1 Location in patent: Page/Page column 214

3
[ 193274-53-2 ]
[ 873-77-8 ]
[ 849106-33-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With ammonium chloride In tetrahydrofuran; hexane; ethyl acetate	481.3 Step 3: Step 3: 4-(4-Chloro-phenyl)-4-hydroxy-3-methyl-piperidine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester 3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl ester 3-methyl ester (1.1 g, 4.07 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added 4-chlorophenyl magnesium bromide (12.2 mL, 12.2 mmol) dropwise over ~1/2 h and then stirred at 0°° C. for 1 h. The reaction was quenched with saturated solution of NH4Cl and extracted with ethyl acetate (3*). The organics were collected, dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (10% ethyl acetate/90% hexane to 20% ethyl acetate/80% hexane) to yield the title compound (1.1 g, 70%). 1H-NMR (CDCl3): δ 1.17 (s, 3H), 1.44 (s, 9H), 1.55 (m,1H), 1.96 (d, 1H) 3.00 (m, 1H), 3.37 (m, 2H), 3.53 (s, 3H), 3.91 (m, 2H), 4.07 (d, 1H), 7.27 (d, 2H), 7.43 (d, 2H). ESI-MS m/z: 384.1 (M+1), retention time 2.95.
70%	In tetrahydrofuran at 0℃; for 0.1h;	481.3 4-(4-Chloro-phenyl)-4-hydroxy-3-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester Step 3 4-(4-Chloro-phenyl)-4-hydroxy-3-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl ester 3-methyl ester (1.1 g, 4.07 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added 4-chlorophenyl magnesium bromide (12.2 mL, 12.2 mmol) dropwise over ˜½ h and then stirred at 0° C. for 1 h. The reaction was quenched with saturated solution of NH4Cl and extracted with ethyl acetate (3*). The organics were collected, dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (10% ethyl acetate/90% hexane to 20% ethyl acetate/80% hexane) to yield the title compound (1.1 g, 70%). 1H-NMR (CDCl3): δ 1.17 (s, 3H), 1.44 (s, 9H), 1.55 (m, 1H), 1.96 (d, 1H) 3.00 (m, 1H), 3.37 (m, 2H), 3.53 (s, 3H), 3.91 (m, 2H), 4.07 (d, 1H), 7.27 (d, 2H), 7.43 (d, 2H). ESI-MS m/z: 384.1 (M+1), retention time 2.95.

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO LTD; TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2005/70549, 2005, A1
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1 Location in patent: Paragraph 1394

4
[ 193274-53-2 ]
[ 593-56-6 ]
[ 1188337-99-6 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With triethylamine In ethanol; water at 55 - 60℃; for 1.75h;

5
[ 193274-53-2 ]
[ 3332-29-4 ]
[ 1188338-00-2 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With triethylamine In ethanol; water at 55 - 60℃; for 1.75h;

6
[ 193274-53-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In toluene at 140℃; for 5h; Reflux;	14.II II. Step 4B-3 and B-4 A 250 mL of round-bottomed flask equipped with dean-stark condenser was charged with B-2 (3.88 g, 14.2 mmol) and toluene (70 mL). Then to the solution were added benzylamine (1.7 mL, 15.6 mmol) and p-toluenesulfonic acid monohydrate (50 mg, catalytic amount). The resulting mixture was heated under reflux (bath 140 C.) for 5 h. The reaction mixture was concentrated under reduced pressure to yield a yellow solid. The crude solid was dissolved in acetonitrile (35 mL) in a 250 mL of round-bottomed flask. At 0 C., to the solution were added acetic acid (23 mL, 398 mmol) and sodium triacetoxyborohydride (7.94 g, 35.6 mmol) portionwise. The resulting mixture was stirred at 0 C. for 30 min and at room temperature for 1.5 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved with dichloromethane (100 mL) and added with saturated sodium carbonate slowly. Gases released vigorously. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated. The two diastereomers were separated using silica gel column chromatography. The upper isomer was identified as cis (B-3) and the lower isomer was assigned as trans (B-4) after 2D- and NOE NMR study.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2009/325948, 2009, A1 Location in patent: Page/Page column 116-117

7
[ 220389-30-0 ]
[ 74-88-4 ]
[ 193274-53-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In acetone at 70℃; Reflux;	14.I I. Step 3B-2 A mixture of B-1 (7.0 g, 27.2 mmol) [Bioorg. Med. Chem. 2003, 11, 581-590.], potassium carbonate (7.5 g, 54.5 mmol), and iodomethane (3.4 mL, 54.5 mmol) in dry acetone was heated under reflux (70 C. bath) overnight. After completion, the reaction mixture was cooled to ambient temperature. The reaction mixture was filtered through 30 mL/30 M fritted filter to remove salt. The filtrate was concentrated under reduced pressure to yield a brown oil. The crude was purified using silica gel column chromatography to give B-2 as a colorless oil. Yield: 5.53 g (75%)

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2009/325948, 2009, A1 Location in patent: Page/Page column 116-117

8
[ 193274-53-2 ]
[ 1372548-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 4h;	2 To an ice-cold solution of O1-tert-butyl O3-methyl 3-methyl-4-oxo-piperidine-1,3-dicarboxylate (0.5 g, 1.85 mmol) in MeOH (10 mL) was added acetic acid (0.5 mL) followed by portion wise addition of sodium cyanoborohydride (0.12 g, 1.85 mmol). The mixture was stirred at rt for 4 h. After completion of reaction (by TLC), water (50 mL) was added and extracted with DCM (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the product as a viscous liquid (0.5 g). MS: 274.13 [M+H]+.

Reference： [1]Current Patent Assignee: SPERO THERAPEUTICS INC - US2012/88750, 2012, A1 Location in patent: Page/Page column 28; 29

9
[ 24424-99-5 ]
[ 193274-53-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 12 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 2.2: 13.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: dmap / dichloromethane / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 44 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1
[2]Current Patent Assignee: SPERO THERAPEUTICS INC - US2012/88750, 2012, A1

10
[ 71486-53-8 ]
3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-(R,S)-methyl ester [ No CAS ]

Reference： [1]Patent: US2016/31908,2016,A1
[2]Patent: US2012/88750,2012,A1

11
[ 193274-53-2 ]
[ 1159155-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.1 h / 0 °C 2: trifluoroacetic acid / 1 h / 0 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1

12
[ 193274-53-2 ]
[ 849105-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.1 h / 0 °C 2: trifluoroacetic acid / 1 h / 0 °C 3: potassium carbonate / water; acetonitrile / 48 h / 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1

13
[ 193274-53-2 ]
[ 849105-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 0.1 h / 0 °C 2: trifluoroacetic acid / 1 h / 0 °C 3: potassium carbonate / water; acetonitrile / 48 h / 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1

14
[ 193274-53-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 0.1 h / 0 °C 2: trifluoroacetic acid / 1 h / 0 °C 3: potassium carbonate / water; acetonitrile / 48 h / 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C 5: ChiralPak AD colunm / ethanol; methanol; hexane

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO LTD - US2016/31908, 2016, A1

15
[ 193274-53-2 ]
[ 358-23-6 ]
[ 1462381-82-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;	273 Reference Synthesis Example 273 (1094) 3-Methyl 1-tert-butyl 3-methyl-4-[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydropyridine-1,3(6H)-dicarboxylate Reference Synthesis Example 273 (1094) 3-Methyl 1-tert-butyl 3-methyl-4-[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydropyridine-1,3(6H)-dicarboxylate (1095) To a tetrahydrofuran solution of lithium diisopropylamide (6.47 mL, 7.19 mmol), 3-methyl 1-tert-butyl 3-methyl-4-oxopiperidine-1,3-dicarboxylate (1.63 g, 5.99 mmol) was added under nitrogen atmosphere at -78° C. and the resultant mixture was stirred for 30 minutes. To the reaction solution, trifluoromethanesulfonic acid anhydride (1.28 mL, 7.78 mmol) was added and the resultant mixture was stirred for 30 minutes. Thereafter, the temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (714 mg, yield 30%).

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US9403798, 2016, B2 Location in patent: Page/Page column 132

16
[ 193274-53-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium diisopropyl amide / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / water; 1,2-dimethoxyethane / 3 h / 90 °C

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US9403798, 2016, B2

17
[ 193274-53-2 ]
[ 1462381-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium diisopropyl amide / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / water; 1,2-dimethoxyethane / 3 h / 90 °C 3: water; lithium hydroxide / 1,4-dioxane / 90 °C

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US9403798, 2016, B2

18
[ 193274-53-2 ]
[ 1462381-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / water; 1,2-dimethoxyethane / 3 h / 90 °C 3.1: water; lithium hydroxide / 1,4-dioxane / 90 °C 4.1: triethylamine; diphenyl phosphoryl azide / toluene / 0.5 h / 100 °C 4.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US9403798, 2016, B2

19
[ 193274-53-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: toluene-4-sulfonic acid / toluene / 2 h / Reflux; Dean-Stark 2: sodium tris(acetoxy)borohydride; acetic acid / acetonitrile / 2.5 h / 0 - 20 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5: lithium hydroxide; water / tetrahydrofuran / 72 h / 20 °C 6: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide 7: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 20 °C