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

HRID 43796Notes

Reaction equation

HRID 43796 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[F:18])[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]=[CH:16][C:17]=3[F:18])[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 86648746Methyl cis(+/-)-3-(4-amino-3-methoxypiperidin-1-yl)-4-fluorobenzoate

Product 1

HCID 86648745Methyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-fluorobenzoateYield 85%

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-3-(4-amino-3-methoxypiperidin-1-yl)-4-fluorobenzoate obtained in Example (181b) (18 mg, 0.06 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (10.6 mg, 0.06 mmol), WSC hydrochloride (34.9 mg, 0.18 mmol) and HOBt (8.2 mg, 0.06 mmol), to obtain 22.7 mg of the title compound as a pale yellow solid (85%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-1db2c588da8e4402b3ef8b09c9be98ca
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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