1-Hydroxybenzotriazole → tert-Butyl cis(+/-)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

HRID 43486Notes

Reaction equation

HRID 43486 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4][C@H:3]1[O:21][CH3:22].[CH2:23]([C:25]1[NH:29][C:28]([C:30](O)=[O:31])=[N:27][C:26]=1[C:33]([F:36])([F:35])[F:34])[CH3:24].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:23]([C:25]1[NH:29][C:28]([C:30]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=3)[C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:4][C@H:3]2[O:21][CH3:22])=[O:31])=[N:27][C:26]=1[C:33]([F:35])([F:36])[F:34])[CH3:24]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675485585-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid2×HCID 86648499tert-Butyl cis(+/-)-3-(4-amino-3-methoxypiperidin-1-yl)benzoate

Product 1

HCID 86648498tert-Butyl cis(+/-)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoateYield 67%

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-3-(4-amino-3-methoxypiperidin-1-yl)benzoate obtained in Example (42d) (about 0.26 mmol), 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained by the method described in Example (39e) (50 mg, 0.24 mmol), WSC hydrochloride (137 mg, 0.71 mmol) and HOBT (32 mg, 0.24 mmol), to obtain 79.7 mg of the title compound as a white solid (67%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-8a9340cd72d34555b03cc4c4cf4b956e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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