4-Toluenesulfonyl chloride → HCID 59655780, compound

HRID 2054352Notes

Reaction equation

HRID 2054352 reaction equation
[N:1]1[C:14]2[N:8]3[C:9](=[O:13])[NH:10][CH:11]=[CH:12][C:7]3=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C=O)C>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:10]2[CH:11]=[CH:12][C:7]3=[CH:6][C:5]4[CH:4]=[CH:3][CH:2]=[N:1][C:14]=4[N:8]3[C:9]2=[O:13])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 11401184HCID 11401184, compound

Product 1

HCID 59655780HCID 59655780, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cooled (0° C.) solution of 11a (500 mg, 2.7 mmol) in DMF (30 ml), NaH (130 mg, 3.2 mmol) was added. The mixture was stirred for 10 min. and a solution of p-toluensulphonyl chloride (570 mg, 3.0 mmol) in DMF (10 ml) was added. The mixture was stirred at room temperature for 1 h. and quenched with water (1 ml). The solvent was evaporated and the residue dissolved in AcOEt. The organic solution was washed with aq. Na2CO3, evaporated and purified by flash column chromatography. Elution with hexane/CH2Cl2 (1/1) gave 8,9-dihydro-8-(4methylphenylsulfonyl)pyrido[3′,2′:4,5]-pyrrolo[1,2-c]pyrimidin-9-one (360 mg, 40%) as a white solid.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 1 h.
  3. customquenched with water (1 ml)
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in AcOEt
  6. washThe organic solution was washed with aq. Na2CO3
  7. customevaporated
  8. custompurified by flash column chromatography
  9. washElution with hexane/CH2Cl2 (1/1)

Sources & evidence

ORD record
ord-6f2677aeaf1f42dc9b2ffefef7ae0e13
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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