Water → HCID 68921803, compound

HRID 1929741Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:36][CH3:37])=[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.[CH3:38][O-:39].[Na+].C(Cl)(Cl)Cl.O>CO.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:36][CH3:37])=[N:10][C:11]2[N:12]([N:21]=[C:22]([O:39][CH3:38])[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: 100 °C

Procedure

To a solution of the compound obtained in Example 36 (24 mg) in methanol/tetrahydrofuran (2 mL/1 mL) was added sodium methoxide (23 mg) and the mixture was stirred at 100° C. for 2 hours in a microwave reactor. After cooling to room temperature, to the reaction mixture was added chloroform and water and the organic layer was separated and concentrated in vacuo and the resultant crude product was purified by a column chromatography on NH-silica gel (Chromatorex NH-silica gel/Fuji Silicia Chem., solvent; hexane/ethyl acetate=65/35 to 30/70) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)-2,5-dimethoxypyrazolo[1,5-a]pyrimidine (17.8 mg; yield: 81%) as a colorless solid.

Workup

temperatureAfter cooling to room temperature, to the reaction mixture
customthe organic layer was separated
concentrationconcentrated in vacuo
customthe resultant crude product was purified by a column chromatography on NH-silica gel (Chromatorex NH-silica gel/Fuji Silicia Chem., solvent; hexane/ethyl acetate=65/35 to 30/70)

Sources & evidence

ORD record: ord-c1bbc7095f104b8e8e8a8bbf3bea2fe6
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188097B2

Reaction notes

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