Methanol → {1-[4-Chloro-3-(5-methyoxy-1H-benzoimidazol-2-yl)-phenyl]-pyrrolidin-4-yl}-pyrolidin-1-yl-methanone formate

HRID 77096Notes

Reaction equation

HRID 77096 reaction equation
C([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=2[N:10]=[C:9]1[C:19]1[CH:24]=[C:23]([N:25]2[CH2:30]C[CH:28]([C:31]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:32])[CH2:27][CH2:26]2)[CH:22]=[CH:21][C:20]=1[Cl:38])=[O:7])(C)(C)C.ClCCl.CO>Cl.CCOCC>[CH:6]([OH:7])=[O:5].[Cl:38][C:20]1[CH:21]=[CH:22][C:23]([N:25]2[CH2:30][CH:28]([C:31]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:32])[CH2:27][CH2:26]2)=[CH:24][C:19]=1[C:9]1[NH:8][C:12]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=2[N:10]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 669777312-{2-Chloro-5-[4-(pyrrolidine-1-carbonyl)-piperidin-1-yl]-phenyl}-5-methoxy-benzoimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 178488053{1-[4-Chloro-3-(5-methyoxy-1H-benzoimidazol-2-yl)-phenyl]-pyrrolidin-4-yl}-pyrolidin-1-yl-methanone formateYield 33.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Method F—Step b To a mixture of 2-{2-Chloro-5-[4-(pyrrolidine-1-carbonyl)-piperidin-1-yl]-phenyl}-5-methoxy-benzoimidazole-1-carboxylic acid tert-butyl ester (0.10 g, 0.19 mmol) in 2M HCl in Et2O (2 mL), few drops of dichloromethane and methanol were added to improve the solubility of the starting material. The resulting mixture was stirred overnight at room temperature, Et2O was added (5 mL), the precipitate was filtered off and then purified by PrepHPLC to get 0.03 g of the title compound as hydrochloride salt, with quantitative yield.

Workup

  1. filtrationthe precipitate was filtered off
  2. custompurified by PrepHPLC

Sources & evidence

ORD record
ord-2127807db87f4cdb90d66118986c31ac
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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