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

HRID 1424961Notes

Reaction equation

HRID 1424961 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][CH3:17].[CH2:18]([C:20]1[NH:24][C:23]([C:25](O)=[O:26])=[N:22][C:21]=1[C:28]([F:31])([F:30])[F:29])[CH3:19].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:18]([C:20]1[NH:24][C:23]([C:25]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]2[O:15][CH2:16][CH3:17])=[O:26])=[N:22][C:21]=1[C:28]([F:30])([F:31])[F:29])[CH3:19]

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 86648467Tert-butyl cis(+/-)-4-amino-3-ethoxypiperidine-1-carboxylate

Product 1

HCID 86648503tert-Butyl cis(+/-)-4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-4-amino-3-ethoxypiperidine-1-carboxylate obtained in Example (112d) (178 mg, 0.73 mmol), 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained by the method described in Example (39e) (100 mg, 0.48 mmol), WSC hydrochloride (280 mg, 1.46 mmol) and HOBT (66 mg, 0.49 mmol), to obtain 173.5 mg of the title compound as a white foamy substance (91%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-5fc2841515cd48d1a4eb0adc4b025543
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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