Ethyl Acrylate → HCID 67024814, compound

HRID 488427Notes

Reaction equation

HRID 488427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:32][CH2:33][CH:34]4[CH2:36][CH2:35]4)=[C:17]([NH:20][C:21](=[O:31])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH:38]=[CH2:39]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:32][CH2:33][CH:34]4[CH2:35][CH2:36]4)=[C:17]([NH:20][C:21](=[O:31])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][N:28]([CH2:39][CH2:38][C:37]([O:41][CH2:42][CH3:43])=[O:40])[CH2:27][CH2:26]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 53675098HCID 53675098, compound

Product 1

HCID 67024814HCID 67024814, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 200 mg of 4-[(3-chloro-4-fluoro-phenyl)amino]-6-{[4-(piperazin-1-yl)-1-oxo-2-buten-1-yl]amino}-7-cyclopropylmethoxy-quinazoline and 0.11 ml of ethyl acrylate in 2 ml of ethanol is heated under reflux for one hour. The solvent is evaporated in vacuo and the crude product is purified by column chromatography on silica gel with methylene chloride/methanol (95:5 to 90:10) followed by recrystallization from diethyl ether. Yield: 164 mg (69% of theory), Melting point: 183-185° C. Mass spectrum (ESI−): m/z=609, 611 [M−H]−

Workup

  1. temperatureis heated
  2. temperatureunder reflux for one hour
  3. customThe solvent is evaporated in vacuo
  4. customthe crude product is purified by column chromatography on silica gel with methylene chloride/methanol (95:5 to 90:10)
  5. customfollowed by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-aef5de500aa94c18aba7e24e7f3b7400
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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