1-Hydroxybenzotriazole → Ethyl cis(+/-)-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]acetate

HRID 1424988Notes

Reaction equation

HRID 1424988 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:12]=2)[CH2:4][C@H:3]1[O:19][CH3:20].[Cl:21][C:22]1[N:23]=[C:24]([C:29](O)=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:21][C:22]1[N:23]=[C:24]([C:29]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[S:9][CH:10]=[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:12]=3)[CH2:4][C@H:3]2[O:19][CH3:20])=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid2×HCID 86648523Ethyl cis(+/-)-[2-(4-amino-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]acetate

Product 1

HCID 86648524Ethyl cis(+/-)-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]acetateYield 36%

Procedure

The same operation as in Example (1g) was performed using ethyl cis(±)-[2-(4-amino-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]acetate obtained in Example (64d) (about 0.29 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (45 mg, 0.26 mmol), WSC hydrochloride (150 mg, 0.78 mmol) and HOBT (35 mg, 0.26 mmol), to obtain 42.6 mg of the title compound (36%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-3eb93b21a1834faf8799fae16564a12c
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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