Hydrochloric Acid → HCID 68923992, compound

HRID 1929743Notes

Reaction equation

HRID 1929743 reaction equation
[NH2:1][C:2]1[C:24]([C:25](=[O:32])[NH:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:5]2[N:6]=[CH:7][C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].Cl>C(OCC)(=O)C>[C:39]([NH:1][C:2]1[C:24]([C:25](=[O:32])[NH:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:5]2[N:6]=[CH:7][C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:9]([C:10]3[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[N:4]2[N:3]=1)(=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67272527HCID 67272527, compound

Product 1

HCID 68923992HCID 68923992, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the compound obtained in Example 40 (60 mg), pyridine (600 μL) and acetic anhydride (200 μL) was stirred at 100° C. for 3 days. After cooling to room temperature, to the reaction mixture was added an aqueous 1N HCl and ethyl acetate and the mixture was stirred. The extract 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 NH-silica gel (Chromatorex NH-silica gel/Fuji Silicia Chem., solvent; hexane/ethyl acetate=90/10 to 50/50) to give 2-acetylamino-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)pyrazolo[1,5-a]pyrimidine (38.2 mg; yield: 58%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. stirringthe mixture was stirred
  3. dry with materialThe extract was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. 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=90/10 to 50/50)

Sources & evidence

ORD record
ord-4f9fd9b0a72540e3ad6713823425f82d
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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