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 43481Notes

Reaction equation

HRID 43481 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-a683583dfe29401c956bc78a9bf312af
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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