Water → HCID 67431296, compound

HRID 1661354Notes

Reaction equation

HRID 1661354 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[C:8]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH:18]=[C:17]([C:19](Cl)=[O:20])[N:16]=[CH:15]2)[CH:9]=1.O>CN(C=O)C>[C:8]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH:18]=[C:17]([C:19]([N:3]3[CH:7]=[CH:6][CH:5]=[N:4]3)=[O:20])[N:16]=[CH:15]2)[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 24758Sodium hydrideHCID 86634424HCID 86634424, compound

Product 1

HCID 67431296HCID 67431296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred, ice-cooled solution of sodium hydride (45 mg, 1.14 mmol) in anhydrous DMF (10 ml) was added pyrazole (77 mg, 1.14 mmol) and stirring was continued for 30 min. under nitrogen. A solution of compound 11a (0.27 g, 0.95 mmol) in DMF (10 ml) was added slowly and the resultant mixture was stirred at ambient conditions overnight. Water (80 ml) was added and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure and the concentrate was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and petroleum ether (1:1) to afford 178. (60 mg, 20%). Mp 124-127° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe concentrate was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and petroleum ether (1:1)

Sources & evidence

ORD record
ord-8844e27fe7ac41e9aec701578dd435bb
Source dataset
uspto-grants-2011_10
Patent number
US08030339B2

Reaction notes

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