Methyl azetidine-3-carboxylate hydrochloride → Methyl 1-((3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)azetidine-3-carboxylate

HRID 1177435Notes

Reaction equation

HRID 1177435 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[N:13]=2)[CH:5]=O.Cl.[NH:32]1[CH2:35][CH:34]([C:36]([O:38][CH3:39])=[O:37])[CH2:33]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][N:32]2[CH2:35][CH:34]([C:36]([O:38][CH3:39])=[O:37])[CH2:33]2)[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[N:13]=2

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 866387093-Fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Product 1

HCID 67111178Methyl 1-((3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)azetidine-3-carboxylate

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)-benzaldehyde (0.36 g, 0.85 mmol), methyl azetidine-3-carboxylate hydrochloride (0.388 g, 2.56 mmol) according to Reference R and the general procedure for reductive amination to give methyl 1-((3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)azetidine-3-carboxylate as an oil which solidified to a white solid. MS (ESI) m/z: Calculated: 515.2; Observed: 516.1 (M++1).

Sources & evidence

ORD record
ord-f9073f60eaef4439b402151658d71110
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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