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

HRID 43476Notes

Reaction equation

HRID 43476 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][CH3:16].[CH2:17]([C:19]1[NH:23][C:22]([C:24](O)=[O:25])=[N:21][C:20]=1[C:27]([F:30])([F:29])[F:28])[CH3:18].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:17]([C:19]1[NH:23][C:22]([C:24]([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][CH3:16])=[O:25])=[N:21][C:20]=1[C:27]([F:29])([F:30])[F:28])[CH3:18]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57362389(3R,4S)-4-Amino-1-boc-3-methoxypiperidine2×HCID 675485585-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid

Product 1

HCID 86648488tert-Butyl cis(+/-)-4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-4-amino-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1e) (0.26 g, 1.13 mmol), 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained in Example (39e) (117.5 mg, 0.56 mmol), WSC hydrochloride (0.38 g, 1.98 mmol) and HOBT (76 mg, 0.56 mmol), to obtain 0.19 g of the title compound as a white foamy substance (79%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-2b2cebff393d4f908742be85f7b4aa54
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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