Diisopropylethylamine → HCID 57937297, compound

HRID 1435526Notes

Reaction equation

HRID 1435526 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.[CH:34]1([NH:37][C:38]([CH:40]2[O:45][CH2:44][CH2:43][NH2+:42][CH2:41]2)=[O:39])[CH2:36][CH2:35]1.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:42]3[CH2:43][CH2:44][O:45][C@@H:40]([C:38]([NH:37][CH:34]4[CH2:35][CH2:36]4)=[O:39])[CH2:41]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 86615828HCID 86615828, compound

Product 1

HCID 57937297HCID 57937297, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (1.1 g, 2.7 mmol) was added to a solution of 2-[(cyclopropylamino)carbonyl]morpholin-4-ium trifluoroacetate (0.92 g, 3.2 mmol) (see the following step B for preparation) and DIPEA (1.5 mL, 8.1 mmol) in DCE at 80° C. The reaction mixture was stirred for 1 h and washed with saturated NaHCO3 solution, water and brine. The solvent was concentrated to provide the racemic title compound as white solid. The enantiomers were separated by chiral preparative HPLC to provide the title compounds.

Workup

  1. washwashed with saturated NaHCO3 solution, water and brine
  2. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-3d419f51c0534d15ae61c772ea9d6023
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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