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

HRID 1177428Notes

Reaction equation

HRID 1177428 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:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH:22]=[CH:21][CH2:20]1)[N:13]=2)[CH:5]=O.Cl.[NH:31]1[CH2:34][CH:33]([C:35]([O:37][CH3:38])=[O:36])[CH2:32]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][N:31]2[CH2:34][CH:33]([C:35]([O:37][CH3:38])=[O:36])[CH2:32]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:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:20][CH:21]=[CH:22][CH2:23]1)[N:13]=2

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 866387083-Fluoro-4-(5-(1-phenylcyclopent-3-enyl)-thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Product 1

HCID 67111616Methyl 1-((3-fluoro-4-(5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)azetidine-3-carboxylate

Procedure

Reaction of 3-fluoro-4-(5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine-2-yl)-benzaldehyde (0.48 g, 1.2 mmol), methyl azetidine-3-carboxylate hydrochloride (0.365 g, 2.41 mmol) according to Reference R and the general procedure for reductive amination gave methyl 1-((3-fluoro-4-(5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)azetidine-3-carboxylate as an oil which partially solidified to a white solid. MS (ESI) m/z: Calculated: 499.0; Observed: 500.1 (M++1).

Sources & evidence

ORD record
ord-10a14c6baef6452aa13efef163eb6782
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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