Dimethylformamide → N-[3-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-4-chloro-benzenesulfonamide

HRID 655841Notes

Reaction equation

HRID 655841 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([NH2:17])=[C:11]3[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.CN(C=O)C>CO>[NH2:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:4]3[CH:3]=[C:2]([NH:1][S:25]([C:22]4[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=4)(=[O:27])=[O:26])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 119961041-(3-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 57750243N-[3-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-4-chloro-benzenesulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11B, 1-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (40 mg, 1.1 eq, 0.18 mmol), 4-chlorobenzenesulphonylchloride (34 mg, 1.0 eq, 0.16 mmol) and diisopropylethylamine (28 μl, 1.0 eq, 0.16 mmol) were added to DMF (1 ml) and the mixture was stirred for 18 hours at room temperature under an inert atmosphere. Methanol was then added (1 ml) and the solvents were removed in vacuo. The resultant oil was purified by semi-preparative HPLC to yield the title compound as a white solid (45 mg, 0.11 mmol, 70%). LCMS: [M+H]+=401, Rt=1.80 min, 100% purity.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe resultant oil was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-021b363ba85949b28b59486293a84222
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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