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

HRID 655843Notes

Reaction equation

HRID 655843 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.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=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:26]([C:23]4[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=4)(=[O:28])=[O:27])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 119961041-(3-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 57750254N-[3-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-4-methoxy-benzenesulfonamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11B, 1-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (36 mg, 1.1 eq, 0.16 mmol), 4-methoxybenzenesulphonylchloride (30 mg, 1.0 eq, 0.15 mmol) and diisopropylethylamine (25 μl, 1.0 eq, 0.15 mmol) were added to DMF (1 ml) and the mixture was stirred for 15 hours at room temperature under an inert atmosphere. Methanol was then added (1 ml) and the solvents were removed in vacuo. The resultant solid was purified by semi-preparative HPLC to yield the title compound as a white solid (30 mg, 0.08 mmol, 52%). LCMS: [M+H]+=397, Rt=1.68 min, 100% purity.

Workup

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

Sources & evidence

ORD record
ord-6962edaaced3438195932c1782fab6c4
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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