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

HRID 655853

Reaktionsgleichung

Reaktionsgleichung von HRID 655853
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ef23fd5852aa4ebea4b90e3e3903faa9
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071607B2

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