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

HRID 655844Notes

Reaction equation

HRID 655844 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=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:4]3[CH:3]=[C:2]([NH:1][S:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)(=[O:25])=[O:24])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 119961041-(3-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 57750250Thiophene-2-sulfonic Acid [3-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amideYield 18.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11B, 1-(3-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 (10 mg, 0.03 mmol, 16%). LCMS: [M+H]+=373, Rt=1.63 min, 100% purity.

Workup

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

Sources & evidence

ORD record
ord-9594e0134fde44e29dfdfe27e73ab77b
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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