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

HRID 43782Notes

Reaction equation

HRID 43782 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([F:18])[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[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]([CH:15]=[C:16]([F:18])[CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])[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 86648731Methyl cis(+/-)-3-(4-amino-3-methoxypiperidin-1-yl)-5-fluorobenzoate

Product 1

HCID 86648730Methyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-fluorobenzoateYield 78%

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-3-(4-amino-3-methoxypiperidin-1-yl)-5-fluorobenzoate obtained in Example (175b) (50.6 mg, 0.18 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (28 mg, 0.16 mmol), WSC hydrochloride (93.7 mg, 0.49 mmol) and HOBt (22 mg, 0.16 mmol), to obtain 56 mg of the title compound as a pale yellow solid (78%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-ed680931263e45a39b9ebd6ffdc058d4
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…