Citric Acid → 2-cyano-3-(7-ethoxalylamino-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide

HRID 21550Notes

Reaction equation

HRID 21550 reaction equation
[NH2:1][C:2]1[CH:33]=[C:32]2[C:5]([CH2:6][C:7]3[C:11]([C:12](=[O:25])[CH:13]([C:23]#[N:24])[C:14]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:15])=[N:10][N:9]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:8]=32)=[CH:4][CH:3]=1.N1[CH:39]=[CH:38]C=CC=1.C(O)(=O)C[C:42](CC(O)=O)([C:44]([OH:46])=[O:45])[OH:43]>CN(C)C=O>[C:23]([CH:13]([C:12]([C:11]1[C:7]2[CH2:6][C:5]3[C:32](=[CH:33][C:2]([NH:1][C:42]([C:44]([O:46][CH2:38][CH3:39])=[O:45])=[O:43])=[CH:3][CH:4]=3)[C:8]=2[N:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:10]=1)=[O:25])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15])#[N:24]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 1049PyridineHCID 19932636HCID 19932636, compound

Product 1

HCID 867487252-cyano-3-(7-ethoxalylamino-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(7-Amino-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl) -2-cyano-3-oxo-N-phenyl-propanamide (1.1 g) dissolved in anhydrous dimethylformamide (70 ml) containing pyridine (1 ml) is reacted with ethyl oxalyl chloride (0.7 g) under stirring at room temperature for 6 hours. The reaction mixture is diluted with ice water and acidified to pH 4 with citric acid. The precipitate is filtered and washed with water. Crystallization from CHCl3 /ethanol yields 1.1 g of 2-cyano-3-(7-ethoxalylamino -1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl) -3-oxo-N-phenyl-propanamide.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with water
  3. customCrystallization from CHCl3 /ethanol

Sources & evidence

ORD record
ord-ed4867c870c14633bde40ee80d28f31a
Source dataset
uspto-grants-1995_06
Patent number
US05424308

Reaction notes

Loading…