4-t-Butylbenzenesulfonyl chloride → HCID 71731560, compound

HRID 1406545Notes

Reaction equation

HRID 1406545 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([N:25]2[C:29]([NH2:30])=[CH:28][C:27]([CH3:31])=[N:26]2)=[CH:17][N:16]=1>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:30][C:29]2[N:25]([C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:15]=[N:16][CH:17]=3)[N:26]=[C:27]([CH3:31])[CH:28]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 86694512HCID 86694512, compound

Product 1

HCID 71731560HCID 71731560, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-t-butylbenzenesulfonyl chloride (0.10 g, 0.43 mmol) and 1-(isoquinolin-4-yl)-3-methyl-1H-pyrazol-5-amine (0.080 g, 0.36 mmol) in pyridine (5 mL) was heated at 80° C. for 15 h with stirring. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 50-100% ethyl acetate in hexanes) to give the title compound as a white solid (0.18 g, 0.12 mmol, 27%). 1H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.02 (s, 1H), 8.87 (dd, J=1.6, 6.8 Hz, 1H), 7.58-7.53 (m, 2H), 7.58 (s, 1H), 7.56 (s, 1H), 7.39-7.35 (m, 3H), 6.25 (s, 1H), 2.34 (s, 3H), 1.32 (s, 9H); MS: (ES) m/z calculated for C23H25N4O2S [M+H]+ 421.2. found 422.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe crude residue was purified by flash chromatography (SiO2, 50-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d60141cdb92d420ead53f817cc4fc63d
Source dataset
uspto-grants-2014_12
Patent number
US08916601B2

Reaction notes

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