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

HRID 655856Notes

Reaction equation

HRID 655856 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.[S:18]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19]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:23]([C:20]4[CH:21]=[CH:22][S:18][CH:19]=4)(=[O:25])=[O:24])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2776378Thiophene-3-sulfonyl ChlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 11996712Thiophene-3-sulfonic Acid [4-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amideYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (39 mg, 1.0 eq, 0.17 mmol), 3-thiophenesulphonylchloride (31 mg, 1.0 eq, 0.17 mmol) and diisopropylethylamine (30 μl, 1.0 eq, 0.17 mmol) were added to DMF (1 ml) and the mixture was stirred for 18 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 absorbed onto silica and purified by column chromatography using DCM/MeOH (96:4) as eluent to yield the title compound as a white solid (13 mg, 0.03 mmol, 20%). LCMS: [M+H]+=373, Rt=1.60 min, 100% purity.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe resultant residue was absorbed onto silica
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-366bc59bdb814ee491621a1c47f7025b
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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