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

HRID 1425243Notes

Reaction equation

HRID 1425243 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([CH3:14])=[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:15]([O:17][CH3:18])=[O:16])[C:11]([CH3:14])=[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 86648721Methyl cis(+/-)-5-(4-amino-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylate

Product 1

HCID 86648720Methyl cis(+/-)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylate

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-5-(4-amino-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylate obtained in Example (171b) (113 mg, 0.4 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (64 mg, 0.37 mmol), WSC hydrochloride (211 mg, 1.1 mmol) and HOBt (49.7 mg, 0.37 mmol), to obtain 18.0 mg of the title compound as a pale yellow oily substance (11%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-90439962887d44aca8f0c351023ddd1a
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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