Sodium hydride → HCID 56592413, compound

HRID 1616090Notes

Reaction equation

HRID 1616090 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:14]2[NH:21][CH:20]=[C:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[C:15]=2[N:16]=[CH:17][N:18]=1.[H-].[Na+].[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:14]2[N:21]([S:38]([CH3:37])(=[O:40])=[O:39])[CH:20]=[C:19]([CH:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]3)[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 56592412HCID 56592412, compound

Product 1

HCID 56592413HCID 56592413, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-(4-{[2-fluoro-4-(methylsulfonyl)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (3.1 mg, 0.0063 mmol) was dissolved in N,N-dimethylformamide (0.5 mL), sodium hydride (55% in oil, 0.4 mg, 0.0095 mmol) and methanesulfonyl chloride (0.4 mL, 0.0057 mmol) were added under ice-cooling, followed by stirring at room temperature for 3 hours. The reaction liquid was diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified by using silica gel chromatography (chloroform:methanol=10:1) to give the titled compound (0.6 mg, 16.8%) as a pale yellow amorphous.

Workup

  1. temperaturecooling
  2. customThe reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-f47ed2adcce34b8187ea8131f97f4dfc
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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