N,N-Dimethylethylenediamine → HCID 59700622, compound

HRID 902027Notes

Reaction equation

HRID 902027 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([N:12]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:11]=1)=O)C.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33]>>[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH:33][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([N:12]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:11]=1)=[O:3]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 69221865HCID 69221865, compound

Product 1

HCID 59700622HCID 59700622, compoundYield 10%

Procedure

Heat 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-6-carboxylic acid ethyl ester (75 mg, 0.2 mmol) in 2 ml of N,N-dimethylethylenediamine at 90° C. for 6 hr in a sealed glass tube with stirring. Extract reaction solution once with water/methylene chloride and concentrate the organic layer in vacuo. Purify using preparative TLC (Silica Gel, 90:10 methylene chloride/methanol) to give 12 mg (10%) of the title compound MS ES+ m/e 418.2 (M+1).

Workup

  1. extractionExtract
  2. customreaction solution once with water/methylene chloride
  3. concentrationconcentrate the organic layer in vacuo
  4. customPurify

Sources & evidence

ORD record
ord-eea7a719f84e4627856e8fe028358355
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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