2,2,2-Trifluoroethanol → HCID 178432260, compound

HRID 513845Notes

Reaction equation

HRID 513845 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20](S)[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23](C)[CH:22]=2)=[O:18].O[O:31][S:32]([O-:34])=O.[K+].[CH2:36](O)C(F)(F)F>>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([S:32]([CH3:36])(=[O:34])=[O:31])[CH:22]=2)=[O:18]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 23707502Potassium hydroxy sulfiteHCID 178422724HCID 178422724, compound

Product 1

HCID 178432260HCID 178432260, compound

Procedure

[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(6-methyl-sulfanyl-1H-indol-2-yl)-methanone (23 mg, 0.057 mmol) was dissolved in trifluoroethanol (5 ml), and an aqueous solution (0.5 ml) of oxone (105 mg, 0.171 mmol) was added thereto. The mixture was stirred at room temperature under a nitrogen atmosphere for 1.75 hours. The reaction mixture was filtered, and the filtrate was concentrated. The resulting residue was purified by amino gel column chromatography (dichloromethane/methanol=99/1 to 92/8). Thus, [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(6-methanesulfonyl-1H-indol-2-yl)-methanone was obtained as a pale yellow solid (8 mg, 32%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by amino gel column chromatography (dichloromethane/methanol=99/1 to 92/8)

Sources & evidence

ORD record
ord-488d9a88e7f84c7f837119e2d82351e0
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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