Dimethylformamide → Thiophene-2-sulfonic Acid [4-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amide

HRID 655853

반응식

HRID 655853 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.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[S:23](Cl)(=[O:25])=[O:24].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:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)(=[O:25])=[O:24])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

생성물 1

HCID 11996552Thiophene-2-sulfonic Acid [4-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amide수율 75%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (36 mg, 1.1 eq, 0.16 mmol), 2-thiophenesulphonylchloride (29 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 15 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 by semi-preparative HPLC to yield the title compound as a white solid (35 mg, 0.09 mmol, 75%). LCMS: [M+H]+=373, Rt=1.60 min, 100% purity.

후처리

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

출처 및 근거

ORD 기록
ord-ef23fd5852aa4ebea4b90e3e3903faa9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071607B2

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