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

HRID 655855

반응식

HRID 655855 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ba642d489c804223a93dd2a4954d93bf
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071607B2

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