2-Fluoro-5-methylbenzenesulfonyl chloride → HCID 178426036, compound

HRID 1508008Notes

Reaction equation

HRID 1508008 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]3[NH:15][N:16]=[C:17]([NH2:18])[C:12]3=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.N1C=CC=CC=1>[NH2:18][C:17]1[C:12]2[C:13](=[N:14][C:9]([C:6]3[CH:7]=[CH:8][C:3]([NH:2][S:27]([C:21]4[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:20]=4[F:19])(=[O:28])=[O:29])=[CH:4][CH:5]=3)=[CH:10][N:11]=2)[NH:15][N:16]=1

Participants

5

Reactant 2

HCID 27827792-Fluoro-5-methylbenzenesulfonyl chlorideHCID 178479031HCID 178479031, compound

Product 1

HCID 178426036HCID 178426036, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 500 mg of 6-(4-amino-phenyl)-1H-pyrazolo[3,4-b]pyrazin-3-ylamine hydrochloride and 397 mg of 2-fluoro-5-methyl-benzenesulfonyl chloride in 4 ml DCM, 0.16 ml pyridine were added and the reaction mixture was stirred for 16 h at RT. Then, the solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 220 mg.

Workup

  1. customThen, the solvents were removed under reduced pressure
  2. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc
  3. additionThe fractions containing the product
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-8440204b49c64ee2812c05e57c234b0c
Source dataset
uspto-grants-2015_12
Patent number
US09221828B2

Reaction notes

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