Acetic Acid → HCID 66991994, compound

HRID 557438Notes

Reaction equation

HRID 557438 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.O=[C:16]([CH3:27])[CH2:17][C:18]([O:20][CH:21]([CH3:26])[C:22]([F:25])([F:24])[F:23])=[O:19].[NH2:28]/[C:29](/[CH3:33])=[CH:30]\[C:31]#[N:32].C(O)(=O)C>CC(O)C>[C:31]([C:30]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:17]([C:18]([O:20][CH:21]([CH3:26])[C:22]([F:25])([F:24])[F:23])=[O:19])=[C:16]([CH3:27])[NH:28][C:29]=1[CH3:33])#[N:32]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 57438897HCID 57438897, compound

Product 1

HCID 66991994HCID 66991994, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

60 mg (0.31 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 63 mg (0.32 mmol) of 2,2,2-trifluoro-1-methylethyl 3-oxobutanoate, 26 mg (0.32 mmol) of 3-amino-crotononitrile and 18 μl (0.32 mmol) of acetic acid in 2 ml of 2-propanol and heated under reflux under argon for 4 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 89 mg (64% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-36f2699202c242bb99b89eb8d7defecf
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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