3,4-Dichlorobenzaldehyde → 7-(3,4-dichlorophenyl)-N-(4-methoxyphenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-sulfonamide

HRID 1786140Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH2:13][C:14](=O)[CH3:15])(=[O:12])=[O:11])=[CH:5][CH:4]=1.[CH3:17][C:18]1[CH:22]=[C:21]([NH2:23])[NH:20][N:19]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH:28]=O>C1COCC1.N1CCCCC1>[Cl:24][C:25]1[CH:26]=[C:27]([CH:28]2[N:20]3[N:19]=[C:18]([CH3:17])[CH:22]=[C:21]3[NH:23][C:14]([CH3:15])=[C:13]2[S:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:12])=[O:11])[CH:30]=[CH:31][C:32]=1[Cl:33]

Participants

Conditions

Temperature: 70 °C

Procedure

N-(4-Methoxyphenyl)-2-oxopropane-1-sulfonamide (100 mg, 0.41 mmol, from Step C), 3-methyl-1H-pyrazol-5-amine (40 mg, 0.41 mmol) and 3,4-dichlorobenzaldehyde (72 mg, 0.41 mmol) were dissolved in THF (6 mL), to which was added a catalytic amount of piperidine (3 drops). The reaction in a sealed tube was stirred at 70° C. for about 36 hrs. After cooling to rt., solvent was removed and crude product was purified by HPLC (acetonitrile-water, 5% to 95% gradient) to provide pure product 7-(3,4-dichlorophenyl)-N-(4-methoxyphenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-sulfonamide as a solid. LC-MS found: (M+1)+=479.21.

Workup

customThe reaction in a sealed tube
temperatureAfter cooling to rt
custom, solvent was removed
customcrude product was purified by HPLC (acetonitrile-water, 5% to 95% gradient)

Sources & evidence

ORD record: ord-8abaf50504aa403d8f2b6fc8485240d7
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507730B2

Reaction notes

Loading…