Methanol → HCID 66751678, compound

HRID 2043342Notes

Reaction equation

HRID 2043342 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:7]([F:14])=[C:8]([NH2:13])[CH:9]=[CH:10][C:11]=1[F:12].[CH3:15][N:16]([CH3:27])[S:17]([N:20]1[CH:24]=[C:23](C=O)[N:22]=[CH:21]1)(=[O:19])=[O:18].[BH4-].[Na+].[CH3:30]O>>[CH3:15][N:16]([CH3:27])[S:17]([N:20]1[C:24]([CH2:30][NH:13][C:8]2[CH:9]=[CH:10][C:11]([F:12])=[C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)[C:7]=2[F:14])=[CH:23][N:22]=[CH:21]1)(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 103979664-Formyl-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 66751330HCID 66751330, compound

Product 1

HCID 66751678HCID 66751678, compoundYield 76%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-[1,3]dioxolan-2-yl-2,4-difluoro-phenylamine (0.41 g, 1.94 mmol) in methanol (10 ml) was added 4-formyl-imidazole-1-sulfonic acid dimethylamide (0.46 g, 2.24 mmol) and the mixture was heated at 60° C. for 18 h. After cooling to room temperature sodium borohydride (0.39 g, 10.3 mmol) was added and the mixture stirred at room temperature for 2 h. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: ethyl acetate/cyclohexane gradient) to yield a light brown gum (604 mg, 76%); MS (ISP): 389.1 ((M+H)+.).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: ethyl acetate/cyclohexane gradient)

Sources & evidence

ORD record
ord-8e6423398ebe4871819996304ff13d4f
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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