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

HRID 1425254Notes

Reaction equation

HRID 1425254 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([F:18])=[C:12]([CH:17]=2)[C:13]([O:15][CH3:16])=[O:14])[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]=[CH:10][C:11]([F:18])=[C:12]([CH:17]=3)[C:13]([O:15][CH3:16])=[O:14])[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 86648734Methyl cis(+/-)-5-(4-amino-3-methoxypiperidin-1-yl)-2-fluorobenzoate

Product 1

HCID 86648733Methyl cis(+/-)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-fluorobenzoateYield 39%

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-5-(4-amino-3-methoxypiperidin-1-yl)-2-fluorobenzoate obtained in Example (176b) (20.1 mg, 0.07 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (11.3 mg, 0.06 mmol), WSC hydrochloride (37.2 mg, 0.19 mmol) and HOBt (8.7 mg, 0.06 mmol), to obtain 11 mg of the title compound as a pale yellow solid (39%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-9e8b08c3b65d4df9be2beabe1cad6205
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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