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Methanesulfonic Acid → HCID 24772844, compound

HRID 1696174
Notes
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Reaction equation

HRID 1696174 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 24772730HCID 24772730, compound

Product 1

HCID 24772844HCID 24772844, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterCatalyst
HCID 6344
Dichloromethane
Solvent
2×

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

  1. stirringAfter stirring
  2. customthe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes