Dimethylformamide → 1-Methyl-1H-imidazole-4-sulfonic Acid [4-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amide

HRID 655855

Reaction equation

HRID 655855 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.C[N:19]1C=CN=[C:20]1[S:24](Cl)(=[O:26])=[O:25].C(N(C(C)C)CC)(C)C.[CH3:37][N:38]([CH:40]=O)[CH3:39]>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:24]([C:20]4[N:19]=[CH:37][N:38]([CH3:39])[CH:40]=4)(=[O:26])=[O:25])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 116583831-Methyl-1H-imidazole-2-sulfonyl chlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 119965511-Methyl-1H-imidazole-4-sulfonic Acid [4-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amideYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (33 mg, 1.0 eq, 0.15 mmol), 1-methylimidazole sulphonylchloride (22 mg, 1.0 eq, 0.15 mmol) and diisopropylethylamine (23 μl, 0.9 eq, 0.13 mmol) were added to DMF (1 ml) and the mixture was stirred for 48 hours at room temperature under an inert atmosphere. Methanol was then added (1 ml) and the solvents were removed in vacuo. The resultant residue was purified column chromatography using DCM/MeOH (96:4) as eluen followed by trituration in methanol to yield the title compound as a white solid (6 mg, 0.03 mmol, 11%). LCMS: [M+H]+=371, Rt=1.33 min, 100% purity.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe resultant residue was purified column chromatography

Sources & evidence

ORD record
ord-ba642d489c804223a93dd2a4954d93bf
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Linked notes

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