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

HRID 1425227Notes

Reaction equation

HRID 1425227 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=2)[CH2:4][C@H:3]1[O:18][CH3:19].[Cl:20][C:21]1[N:22]=[C:23]([C:28](O)=[O:29])[NH:24][C:25]=1[CH2:26][CH3:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:20][C:21]1[N:22]=[C:23]([C:28]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:9]=3)[CH2:4][C@H:3]2[O:18][CH3:19])=[O:29])[NH:24][C:25]=1[CH2:26][CH3:27]

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 86648700Methyl cis(+/-)-4-(4-amino-3-methoxypiperidin-1-yl)pyridine-2-carboxylate

Product 1

HCID 86648701Methyl cis(+/-)-4-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-2-carboxylate

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-4-(4-amino-3-methoxypiperidin-1-yl)pyridine-2-carboxylate obtained in Example (160c) (21.2 mg, 0.08 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (14 mg, 0.08 mmol), WSC hydrochloride (45.98 mg, 0.24 mmol) and HOBt (10.81 mg, 0.08 mmol), to obtain 13.8 mg of the title compound as a white solid.

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-87ae2e19adf14262aa3ca6814e360de1
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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