Methanesulfonic Acid → HCID 24772844, compound

HRID 1696174Notes

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]=[CH:22][C:23]=2[C:24](=[O:34])[NH:25][C:26]2([C:32]#[N:33])[CH2:31][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.CS(O)(=O)=[O:37].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:32]([C:26]1([NH:25][C:24]([C:23]2[CH:22]=[N:21][N:12]3[C:13]([C:14]4[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=4)=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH:9]=[N:10][C:11]=23)=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=[O:37])[NH2:33]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of the compound obtained in Example A1 (70 mg) in methylene chloride (1.0 mL) were added methanesulfonic acid (84 μL) and a few drops of water, and the mixture was stirred at room temperature overnight and at 35° C. for 4 hours. To the reaction mixture was added successively an aqueous saturated sodium hydrogencarbonate solution and methylene chloride. After stirring, the organic layer was separated and concentrated in vacuo. The resultant crude product was purified by column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 95/5) to give 3-[N-(1-carbamoylcyclohexyl)carbamoyl]-6-(2-chlorophenyl)-7-(4-chlorophenyl)-pyrazolo[1,5-a]pyrimidine (18 mg; yield: 25%) as a pale yellow solid.

Workup

stirringAfter stirring
customthe organic layer was separated
concentrationconcentrated in vacuo
customThe resultant crude product was purified by column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 95/5)

Sources & evidence

ORD record: ord-98348fab02934024830e47a3b65f04e5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163759B2

Reaction notes

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