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

HRID 74458Notes

Reaction equation

HRID 74458 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-96fa63a35e3a4c94aa3cdd1b39942b6e
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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