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

HRID 1425230Notes

Reaction equation

HRID 1425230 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:12][CH:13]=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[CH:9]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:12][CH:13]=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 86648704Ethyl cis(+/-)-5-(4-amino-3-methoxypiperidin-1-yl)pyridine-3-carboxylate

Product 1

HCID 86648703Ethyl cis(+/-)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-3-carboxylate

Procedure

The same operation as in Example (1g) was performed using ethyl cis(±)-5-(4-amino-3-methoxypiperidin-1-yl)pyridine-3-carboxylate obtained in Example (162b) (137.5 mg, 0.49 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (82 mg, 0.47 mmol), WSC hydrochloride (270 mg, 1.41 mmol) and HOBt (63.4 mg, 0.47 mmol), to obtain 132 mg of the title compound as a pale yellow oily substance (65%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-37604ae4afe84f3ab937dfcefba86e44
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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