(4-Chlorophenyl)methanesulfonyl chloride → HCID 68323916, compound

HRID 573697Notes

Reaction equation

HRID 573697 reaction equation
[CH3:1][C:2]1[S:12][C:5]2[N:6]=[C:7]([CH3:11])[CH:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:31][C:32]1[CH:42]=[CH:41][C:35]([CH2:36][S:37](Cl)(=[O:39])=[O:38])=[CH:34][CH:33]=1>C1COCC1.O>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:36][S:37]([NH:10][C:9]2[CH:8]=[C:7]([CH3:11])[N:6]=[C:5]3[S:12][C:2]([CH3:1])=[C:3]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=4)[C:4]=23)(=[O:39])=[O:38])=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 227304(4-Chlorophenyl)methanesulfonyl chloride2×HCID 2733832Lithium Hexamethyldisilazide2×HCID 68323863HCID 68323863, compound

Product 1

HCID 68323916HCID 68323916, compoundYield 13.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (100 mg, 0.352 mmol) (Description 4) in THF (2 mL) cooled in an ice bath was added LiHMDS (1M solution in THF) (0.774 mL, 0.774 mmol). The reaction mixture was stirred at RT for 45 min before the addition of 4-chlorobenzylsulfonyl chloride (198 mg, 0.879 mmol). The reaction mixture was then stirred at RT for a further 16 h and was then cooled in an ice bath before the addition of LiHMDS (1M solution in THF) (0.352 mL, 0.352 mmol). The reaction mixture was stirred at RT for 1 h before the addition of 4-chlorobenzylsulfonyl chloride (79.2 mg, 0.352 mmol). The reaction mixture was stirred at RT for a further 16 h and then diluted with water (10 mL) and the aqueous layer extracted with DCM (3×20 mL). The combined organic extracts were dried over a phase separating column and concentrated. The residue was purified by MDAP (basic conditions), to afford the title compound (22 mg). LCMS (A) m/z: 473 [M+1]+, Rt 1.42 min (basic).

Workup

  1. stirringThe reaction mixture was stirred at RT for a further 16 h
  2. extractionthe aqueous layer extracted with DCM (3×20 mL)
  3. customThe combined organic extracts were dried over a phase
  4. customseparating column
  5. concentrationconcentrated
  6. customThe residue was purified by MDAP (basic conditions)

Sources & evidence

ORD record
ord-55a5462831054be58e18d367d90ded9c
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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