2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → HCID 16045281, compound

HRID 1669769Notes

Reaction equation

HRID 1669769 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3](=O)[C:4](=[CH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[O:22][C:21]([CH3:24])=[CH:20][C:19]2=[O:25])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[NH2:29]/[C:30](/[CH3:37])=[CH:31]\[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CC(O)C>[C:5]([C:4]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:30]([CH3:37])[NH:29][C:3]=1[C:2]([F:28])([F:1])[F:27])(=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 67343678HCID 67343678, compound

Product 1

HCID 16045281HCID 16045281, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 410 mg (1.06 mmol) of 4,4,4-trifluoro-2-[(2-methyl-4-oxo-4H-chromen-8-yl)-methylene]-1-phenylbutane-1,3-dione in 10 ml of 2-propanol is mixed with 137.3 mg (1.06 mmol) of ethyl 3-aminocrotonate and stirred under reflux for 12 h. After cooling, the reaction mixture is concentrated, and the residue is taken up in 5 ml of acetic acid and again stirred under reflux for 12 h. The reaction solution is concentrated and the residue is purified by preparative HPLC. 160.3 mg (30.3% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated
  4. stirringagain stirred
  5. temperatureunder reflux for 12 h
  6. concentrationThe reaction solution is concentrated
  7. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-1b0e84858d5a44608f2d502e396f16b7
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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