Water → 1-(4-methoxyphenyl)-3-(methylsulfonyl) 1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 971136Notes

Reaction equation

Cl[C:2]1[C:3](=[O:8])[NH:4][CH2:5][CH2:6][CH:7]=1.Cl/[C:10](=[N:15]\[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)/[S:11]([CH3:14])(=[O:13])=[O:12].CCN(CC)CC.O>C1(C)C=CC=CC=1.CCOC(C)=O.C(Cl)Cl>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([N:16]2[C:2]3[C:3](=[O:8])[NH:4][CH2:5][CH2:6][C:7]=3[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:15]2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Part A. 3-Chloro-5,6-dihydro-2(1H)-pyridinone (10.0 g, 38.17 mmol) and (1Z)-1-[chloro(methylsulfonyl)methylene]-2-(4-methoxyphenyl)hydrazine (5.0 g, 38.17 mmol) were stirred in toluene (200 mL) at RT under N2. Et3N (30 mL, 215.24 mmol) in toluene (150 mL) was added dropwise to the solution. After addition, the mixture was heated at 85° C. overnight. After cooling, H2O was added. It was extracted with EtOAc (2×). The organic layers were washed with H2O (2×) and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2, then CH2Cl2:EtOAc=1:1, then EtOAc) to give 1-(4-methoxyphenyl)-3-(methylsulfonyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (3.85 g, yield: 31%). LC/MS (ESI+) 322.4 (M+H)+, tR=1.79 min (10–90% CH3CN/H2O in a 4-min run).

Workup

additionAfter addition
temperatureAfter cooling
extractionIt was extracted with EtOAc (2×)
washThe organic layers were washed with H2O (2×) and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by flash column chromatography (silica gel, CH2Cl2

Sources & evidence

ORD record: ord-043fe4a4b0b84d588466a5d7a1ce95a0
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312214B2

Reaction notes

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