Water → HCID 86686796, compound

HRID 1403157Notes

Reaction equation

HRID 1403157 reaction equation
[CH:1]1([S:6][CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[C:17]3[CH:25]([F:27])[F:26])[N:13]=[C:12]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:42])C=1.O>C(Cl)Cl>[CH:1]1([S:6]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[C:17]3[CH:25]([F:27])[F:26])[N:13]=[C:12]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[N:11]=2)=[O:42])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 86686797HCID 86686797, compound

Product 1

HCID 86686796HCID 86686796, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-(Cyclopentylsulfanyl)ethyl]-4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)-1,3,5-triazin-2-amine (60 mg) was dissolved in methylene chloride (1.2 mL), and m-chloroperbenzoic acid (75% wet) (32 mg) was added thereto at 0° C., followed by stirring for 10 minutes. Water was added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:80, and subsequently chloroform:methanol=98:2-90:10) to obtain N-[2-(cyclopentyl sulfinyl)ethyl]-4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)-1,3,5-triazin-2-amine (53 mg) as a white powder.

Workup

  1. customat 0° C.
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-ad804b88134f4ac48613acca8265b42b
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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