Methanol → HCID 178505075, compound

HRID 1294084Notes

Reaction equation

HRID 1294084 reaction equation
[NH2:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]4[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=4[F:32])=[O:20])=[CH:14][CH:13]=3)=[CH:10][C:4]=2[N:3]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O.CO>N1C=CC=CC=1>[F:32][C:23]1[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:29])[F:30])=[CH:27][C:22]=1[NH:21][C:19]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[NH:6][C:2]([NH:1][S:34]([CH3:33])(=[O:36])=[O:35])=[N:3][C:4]=3[CH:10]=2)=[CH:17][CH:16]=1)=[O:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 178508201HCID 178508201, compound

Product 1

HCID 178505075HCID 178505075, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-amino-5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)aminocarbonylamino)phenoxy)-1H-benzimidazole (the product of Example 22–600 mg) and methanesulfonyl chloride (5 equiv.) in pyridine was stirred at room temperature for 2 days. The resulting mixture was treated with K2C03 (10 equiv.) and H2O (10 mL) and MeOH (10 mL), and heated at 60 C. for 7 days. The crude solid was collected by filtration. Recrystallization from hot MeOH afforded the title compound (280 mg, 40%);

Workup

  1. customwas stirred at room temperature for 2 days
  2. temperatureheated at 60 C
  3. filtrationThe crude solid was collected by filtration
  4. customRecrystallization from hot MeOH

Sources & evidence

ORD record
ord-a79aee888a474af6b9dda945ebef338e
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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