Diisopropylethylamine → (3S)-1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)pyrrolidine-3-carboxylic acid

HRID 1435506Notes

Reaction equation

HRID 1435506 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C([O-])=O.[C:34]([C@H:37]1[CH2:41][CH2:40][NH2+:39][CH2:38]1)([OH:36])=[O:35].CCN(C(C)C)C(C)C>ClCCCl>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23]([N:39]3[CH2:40][CH2:41][C@H:37]([C:34]([OH:36])=[O:35])[CH2:38]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chlorideHCID 86615824HCID 86615824, compound

Product 1

HCID 57937393(3S)-1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (1.2 g, 2.9 mmol) was added to a solution of (3S)-3-carboxypyrrolidinium trifluoroacetate (0.50 g, 2.3 mmol) and DIPEA (3 mL, 17 mmol) in DCE (20 mL) at 80° C. The reaction mixture was stirred for 2 hrs. and the solvent was concentrated. The product was purified by MPLC on silica gel using 30% acetone in DCM containing 1% of AcOH to provide the title compound as white solid. Yield: 600 mg (42%); MS (ESI) (M+H)+=484.1.

Workup

  1. concentrationand the solvent was concentrated
  2. customThe product was purified by MPLC on silica gel using 30% acetone in DCM containing 1% of AcOH

Sources & evidence

ORD record
ord-477b7804b0f74178bc85f4438e0c170b
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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