Methyl azetidine-3-carboxylate hydrochloride → Methyl 1-(4-(5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate

HRID 1177496Notes

Reaction equation

HRID 1177496 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:18]3[N:23]=[C:22]4[S:24][C:25]([C:27]5[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=5[F:35])=[N:26][C:21]4=[CH:20][CH:19]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:37]1[CH2:40][CH:39]([C:41]([O:43][CH3:44])=[O:42])[CH2:38]1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:18]3[N:23]=[C:22]4[S:24][C:25]([C:27]5[CH:34]=[CH:33][C:30]([CH2:31][N:37]6[CH2:40][CH:39]([C:41]([O:43][CH3:44])=[O:42])[CH2:38]6)=[CH:29][C:28]=5[F:35])=[N:26][C:21]4=[CH:20][CH:19]=3)[CH2:17][CH2:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 866387154-(5-(1-(4-(Benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde

Product 1

HCID 67111767Methyl 1-(4-(5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate

Procedure

Synthesized from 4-(5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde (0.224 g, 0.466 mmol) and methyl azetidine-3-carboxylate hydrochloride (0.177 g, 1.17 mmol) according to the general procedure for reductive amination to give methyl 1-(4-(5-(1-(4-(benzyloxy)phenyl)cyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate as a yellow solid. MS (ESI) m/z: calculated: 579.2; Observed: 580.1 (M++1).

Sources & evidence

ORD record
ord-9cc61cd97aa24140a9d66064d2071907
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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