(Bis(2-methoxyethyl)amino)sulfur trifluoride → 6-(1-Acetyl-4,5-dihydro-1H-pyrrol-2-yl)-5-(4-(methanesulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazole

HRID 13389

Reaction equation

HRID 13389 reaction equation
COCCN(S(F)(F)F)CCOC.[C:14]([N:17]1[CH2:21][CH2:20][CH:19](O)[CH:18]1[C:23]1[C:24]([O:38][C:39]2[CH:44]=[CH:43][C:42]([S:45]([CH3:48])(=[O:47])=[O:46])=[CH:41][CH:40]=2)=[CH:25][C:26]2[N:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[NH:28][C:27]=2[CH:37]=1)(=[O:16])[CH3:15]>C(Cl)(Cl)Cl>[C:14]([N:17]1[CH2:21][CH2:20][CH:19]=[C:18]1[C:23]1[C:24]([O:38][C:39]2[CH:40]=[CH:41][C:42]([S:45]([CH3:48])(=[O:46])=[O:47])=[CH:43][CH:44]=2)=[CH:25][C:26]2[N:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[NH:28][C:27]=2[CH:37]=1)(=[O:16])[CH3:15]

Participants

4

Procedure

2 mg of bis(2-methoxyethyl)aminosulfur trifluoride was added to a chloroform (1 ml) solution of 2 mg of 1-acetyl-2-(5-(4-(methanesulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazol-6-yl)pyrrolidin-3-ol diastereomer A obtained in Example 469, and the reaction liquid was stirred at room temperature for 15 minutes. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1) to obtain the entitled compound as a colorless oily substance.

Workup

  1. customA obtained in Example 469
  2. customthe reaction liquid
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1)
  6. customto obtain the entitled compound as a colorless oily substance

Sources & evidence

ORD record
ord-7826d805fa88468484e7350b593a91a7
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

Loading…