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

HRID 1424968Notes

Reaction equation

HRID 1424968 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][CH2:22][CH3:23].[CH2:24]([C:26]1[NH:30][C:29]([C:31](O)=[O:32])=[N:28][C:27]=1[C:34]([F:37])([F:36])[F:35])[CH3:25].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:24]([C:26]1[NH:30][C:29]([C:31]([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][CH2:22][CH3:23])=[O:32])=[N:28][C:27]=1[C:34]([F:36])([F:37])[F:35])[CH3:25]

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 86648508tert-Butyl cis(+/-)-3-(4-amino-3-ethoxypiperidin-1-yl)benzoate

Product 1

HCID 86648507tert-Butyl cis(+/-)-3-(4-{[(5-Ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoateYield 83%

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-3-(4-amino-3-ethoxypiperidin-1-yl)benzoate obtained in Example (48e) (about 0.22 mmol), 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained by the method described in Example (39e) (40 mg, 0.19 mmol), WSC hydrochloride (120 mg, 0.63 mmol) and HOBT (40 mg, 0.30 mmol), to obtain 81.0 mg of the title compound (83%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-469f3260254144489db2c886bd68ca85
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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