Water → HCID 16722330, compound

HRID 1929740Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:21]=[C:22](S(C)(=O)=O)[C:23]=2[C:24](=[O:31])[NH:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.C[O-].[Na+].O.[C:40](OCC)(=[O:42])C>O1CCCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:21]=[C:22]([O:42][CH3:40])[C:23]=2[C:24](=[O:31])[NH:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the compound obtained in Example 33 (100 mg) in tetrahydrofuran/methanol (3 mL/3 mL) was added sodium methoxide (102 mg) and the mixture was stirred at 50° C. overnight. After cooling to room temperature, to the reaction mixture was added water and ethyl acetate and the mixture was stirred. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80/20 to 60/40) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)-2-methoxypyrazol o[1,5-a]pyrimidine (57.2 mg; yield: 63%) as a pale yellow powder.

Workup

temperatureAfter cooling to room temperature, to the reaction mixture
stirringthe mixture was stirred
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80/20 to 60/40)

Sources & evidence

ORD record: ord-a5fc402032f24b00ad591882b9f233d3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188097B2

Reaction notes

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