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

HRID 655852

Reaction equation

HRID 655852 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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:5]3[CH:6]=[CH:7][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:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 11996549N-[4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-4-methoxy-benzenesulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11A, 1-(4-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 (40 mg, 0.10 mmol, 70%). LCMS: [M+H]+=397, Rt=1.66 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-49d20eba6391448b9c6dfd971f459b8a
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Linked notes

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