Sulfuryl chloride → HCID 178493455, compound

HRID 1778795Notes

Reaction equation

HRID 1778795 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH:6]1([N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:18]4[C:26]5[C:21](=[N:22][C:23]([C:27]6[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[C:28]=6[F:37])=[CH:24][CH:25]=5)[N:20](C5CCCCO5)[N:19]=4)[CH:15]=3)[C:10]2=[O:44])[CH2:8][CH2:7]1>C(Cl)Cl.CO>[Cl:4][C:32]1[C:31]([O:33][CH3:34])=[CH:30][C:29]([O:35][CH3:36])=[C:28]([F:37])[C:27]=1[C:23]1[N:22]=[C:21]2[NH:20][N:19]=[C:18]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[C:10](=[O:44])[N:9]([CH:6]3[CH2:8][CH2:7]3)[CH2:17]4)[C:26]2=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 867228742-cyclopropyl-5-[6-(2-fluoro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]isoindolin-1-one

Product 1

HCID 178493455HCID 178493455, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sulfuryl chloride (10. μL, 0.12 mmol) was added to a stirring solution of 2-cyclopropyl-5-[6-(2-fluoro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]isoindolin-1-one (65 mg, 0.12 mmol) in methylene chloride (1 mL). The mixture was stirred at r.t. for 30 min. It was concentrated to dryness. The solid was dissolved in methanol (0.3 mL). To the solution was added a solution of HCl previously prepared from acetyl chloride (0.15 mL) and methanol (0.15 mL). The mixture was stirred at r.t. for 1 h and then diluted with methanol, and purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+=479.1.

Workup

  1. concentrationIt was concentrated to dryness
  2. dissolutionThe solid was dissolved in methanol (0.3 mL)
  3. additionTo the solution was added a solution of HCl
  4. custompreviously prepared from acetyl chloride (0.15 mL) and methanol (0.15 mL)
  5. stirringThe mixture was stirred at r.t. for 1 h
  6. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-7a4b216fefa7435a82be5991428d8e1f
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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