4-Toluenesulfonyl chloride → HCID 58117092, compound

HRID 2066466Notes

Reaction equation

HRID 2066466 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([C:11]2[N:12]=[C:13]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:14]3[S:19][C:18]([CH2:20][OH:21])=[CH:17][C:15]=3[N:16]=2)[CH:3]=1.[H-].[Na+].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C1COCC1.CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=2)(=[O:38])=[O:37])=[C:4]([C:11]2[N:12]=[C:13]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:14]3[S:19][C:18]([CH2:20][O:21][S:36]([C:33]4[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=4)(=[O:38])=[O:37])=[CH:17][C:15]=3[N:16]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 58117129HCID 58117129, compound

Product 1

HCID 58117092HCID 58117092, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of [2-(6-fluoro-1H-indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl]-methanol (0.54 g, 1.41 mmol) in anhydrous THF (20 mL) and DMF (5 mL) was added sodium hydride (60% suspension in mineral oil, 0.34 g, 8.5 mmol). The resulting mixture was stirred at RT for 10 min, then p-toluenesulfonyl chloride (1.08 g, 5.66 mmol) was added and the reaction mixture was heated at 40° C. for 3 h. The resulting solution was partitioned between EtOAc and a saturated aqueous solution of ammonium chloride. The organic layer was isolated, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a white solid (0.60 g, 62%).

Workup

  1. temperaturethe reaction mixture was heated at 40° C. for 3 h
  2. customThe resulting solution was partitioned between EtOAc
  3. customThe organic layer was isolated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-6ddc3a497585417fb528f02daeff6d97
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

Loading…