1-Hydroxybenzotriazole → Methyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoate

HRID 43787Notes

Reaction equation

HRID 43787 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:4][C@H:3]1[O:18][CH2:19][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[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])[CH2:4][C@H:3]2[O:18][CH2:19][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 86648736Methyl cis(+/-)-3-(4-amino-3-ethoxypiperidin-1-yl)benzoate

Product 1

HCID 86648735Methyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoate

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-3-(4-amino-3-ethoxypiperidin-1-yl)benzoate obtained in Example (177a) (24 mg, 0.09 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (15.1 mg, 0.09 mmol), WSC hydrochloride (49.7 mg, 0.26 mmol) and HOBt (11.7 mg, 0.09 mmol), to obtain 17.1 mg of the title compound as a yellow oily substance (46%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-c401f28bfc3942fbad47ef2e9f2fa09d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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