Dimethylformamide → Ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylate

HRID 704630Notes

Reaction equation

HRID 704630 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[N:21]=[C:22]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]4[CH:29]=3)=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=O.[H-].[Na+].CN(C)C=O.[C:37]([O:40][CH2:41][CH3:42])(=[O:39])[CH3:38]>>[CH3:28][C:26]1[CH:25]=[CH:24][N:23]2[CH:29]=[C:20]([C:18]([N:15]3[CH2:16][CH2:17][N:12]([C:5]4[CH:4]=[C:3]([CH:1]=[CH:38][C:37]([O:40][CH2:41][CH3:42])=[O:39])[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=4)[CH2:13][CH2:14]3)=[O:19])[N:21]=[C:22]2[CH:27]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 200728461-(3-Formyl-4-nitrophenyl)-4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)piperazine

Product 1

HCID 54465980Ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylate

Procedure

A mixture of 1-(3-formyl-4-nitrophenyl)-4-(7methylimidazo[1,2-a]pyridine-2-carbonyl)piperazine (22.8 g), triethyl phosphonoacetate (15.6 g), sodium hydride (60% dispersion in mineral oil) (2.92 g) and N,N-dimethylformamide (250 ml) were stirred for 5 hours at ambient temperature. Ethyl acetate (250 ml) was added thereto and the resulting precipitates were collected and washed with ethyl acetate (100 ml) to give ethyl 3-[3-[4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-6-nitrophenyl]acrylate (18.70 g).

Workup

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with ethyl acetate (100 ml)

Sources & evidence

ORD record
ord-b99c112cd162498ea22dfb9dd39ba9d2
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

Loading…