Dimethylformamide → HCID 178516114, compound

HRID 20288Notes

Reaction equation

HRID 20288 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]([NH2:16])=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:4][CH:3]=1.CCN=C=N[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])C.C1C=CC2N([OH:37])N=NC=2C=1.CN([CH:41]=[O:42])C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:15]([NH:16][C:41]([CH:24]3[CH2:23][CH2:22][C:27](=[O:37])[NH:25]3)=[O:42])=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178508056HCID 178508056, compound

Product 1

HCID 178516114HCID 178516114, compound

Procedure

To a stirred solution of 4-amino-1H-pyrazole-3-carboxylic acid (4-fluorophenyl)-amide (Example 2B) (50 mg; 0.23 mmol), EDAC (52 mg; 0.27 mmol) and HOBt (37 mg; 0.27 mmol) in 5 ml of DMF was added 2-oxoproline (33 mg; 0.25 mmol), and the mixture was then left at room temperature overnight. The reaction mixture was evaporated and the residue purified by preparative LC/MS, to give 24 mg of the product as a white solid. (LC/MS: Rt 2.27 [M+H]+ 332).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by preparative LC/MS

Sources & evidence

ORD record
ord-658267d5e5914a0fa418597c7986535f
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Reaction notes

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