1-Hydroxybenzotriazole → Ethyl cis(+/-)-2-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylate

HRID 1424951Notes

Reaction equation

HRID 1424951 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]([CH3:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=2)[CH2:4][C@H:3]1[O:19][CH3:20].[CH2:21]([C:23]1[NH:27][C:26]([C:28](O)=[O:29])=[N:25][C:24]=1[C:31]([F:34])([F:33])[F:32])[CH3:22].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:21]([C:23]1[NH:27][C:26]([C:28]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[S:9][C:10]([CH3:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=3)[CH2:4][C@H:3]2[O:19][CH3:20])=[O:29])=[N:25][C:24]=1[C:31]([F:33])([F:34])[F:32])[CH3:22]

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 86648492Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 86648493Ethyl cis(+/-)-2-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylate

Procedure

The same operation as in Example (1g) was performed using ethyl cis(±)-2-(4-amino-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylate obtained in Example (40e) (44.9 mg, 0.15 mmol), 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained by the method described in Example (39e) (29 mg, 0.14 mmol), WSC hydrochloride (80 mg, 0.42 mmol) and HOBT (20 mg, 0.15 mmol), to obtain 29.2 mg of the title compound as a colorless oily substance (43%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-ada958d51a354a4fa6c56011ae6a524c
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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