Methyl azetidine-3-carboxylate hydrochloride → Methyl 1-((3-fluoro-4-(6-(1-phenylcyclopropyl)benzo[d]thiazol-2-yl)phenyl)methyl)azetidine-3-carboxylate

HRID 1177446Notes

Reaction equation

HRID 1177446 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[CH:18]=[C:17]([C:19]3([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:13]=2[N:14]=1)[CH:5]=O.Cl.[NH:29]1[CH2:32][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:30]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][N:29]2[CH2:32][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:30]2)[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[CH:18]=[C:17]([C:19]3([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:20][CH2:21]3)[CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 866387103-Fluoro-4-(6-(1-phenylcyclopropyl)benzo[d]thiazol-2-yl)benzaldehyde

Product 1

HCID 67111547Methyl 1-((3-fluoro-4-(6-(1-phenylcyclopropyl)benzo[d]thiazol-2-yl)phenyl)methyl)azetidine-3-carboxylate

Procedure

Reaction of 3-fluoro-4-(6-(1-phenylcyclopropyl)benzo[d]thiazol-2-yl)benzaldehyde (0.050 g, 0.13 mmol) and methyl azetidine-3-carboxylate hydrochloride (0.030 g, 0.20 mmol) according to Reference R and general procedure for reductive amination afforded methyl 1-((3-fluoro-4-(6-(1-phenylcyclopropyl)benzo[d]thiazol-2-yl)phenyl)methyl)azetidine-3-carboxylate. MS (ESI) m/z: Calculated: 472.2; Observed: 473.1 (M++1).

Sources & evidence

ORD record
ord-41abe94a05e54a66a0eceacc44dcb729
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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