Ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate → Ethyl cis(+/-)-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]cyclopropanecarboxylate

HRID 1424993Notes

Reaction equation

HRID 1424993 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:19][CH3:20])=[C:16]([Cl:18])[N:17]=2)=[O:12])[C@H:6]([O:21][CH3:22])[CH2:5]1)(=[S:3])[NH2:2].Br[CH2:24][C:25]([C:27]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:29][CH2:28]1)=O>>[Cl:18][C:16]1[N:17]=[C:13]([C:11]([NH:10][C@H:7]2[CH2:8][CH2:9][N:4]([C:1]3[S:3][CH:24]=[C:25]([C:27]4([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:29][CH2:28]4)[N:2]=3)[CH2:5][C@H:6]2[O:21][CH3:22])=[O:12])[NH:14][C:15]=1[CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 11436266Ethyl 1-(2-bromoacetyl)cyclopropanecarboxylateHCID 86648527HCID 86648527, compound2×

Product 1

HCID 86648528Ethyl cis(+/-)-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]cyclopropanecarboxylate

Procedure

The same operation as in Example (22b) was performed using cis(±)-N-(1-carbamothioyl-3-methoxypiperidin-4-yl)-4-chloro-5-ethyl-1H-imidazole-2-carboxamide obtained by the method described in Example (65c) (40 mg, 0.12 mmol) and ethyl 1-(bromoacetyl)cyclopropanecarboxylate obtained according to a method known in the literature (Heterocycles, 63, 3, 2004, 699-706) (60 mg, 0.26 mmol), to obtain 23.5 mg of the title compound as a colorless oily substance (42%).

Workup

  1. customobtained by the method
  2. customobtained

Sources & evidence

ORD record
ord-35084fc3e1f54a9daa84548818cb2327
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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