Ethanol → HCID 67259096, compound

HRID 1467662Notes

Reaction equation

HRID 1467662 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[F:9][C:10]1[CH:20]=[CH:19][C:18](/[CH:21]=[N:22]/[C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH2:25][O:26][C:27]3=[O:32])=[CH:17][C:11]=1[C:12]([N:14]([CH3:16])[CH3:15])=[O:13].[O-:33][CH2:34]C.[Na+].[CH2:37](O)C>C(OCC)(=O)CC>[CH3:16][N:14]([CH3:15])[C:12]([C:11]1[CH:17]=[C:18]([CH:21]2[CH:7]([C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=3)[C:34](=[O:33])[C:24]3[C:28]([C:27]([O:26][CH2:25][CH3:37])=[O:32])=[CH:29][CH:30]=[CH:31][C:23]=3[NH:22]2)[CH:19]=[CH:20][C:10]=1[F:9])=[O:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2723922Sodium ethoxideHCID 178484454HCID 178484454, compound

Product 1

HCID 67259096HCID 67259096, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound 1-methyl-1H-imidazole-2-carbaldehyde (110 mg, 1.0 mmol) and (E)-2-fluoro-N,N-dimethyl-5-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (300 mg, 0.92 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (85 mg, 3.68 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 2.5 hr. The mixture was quenched with water (20 mL) and solvent was removed in vacuum. The residue was dissolved in water and extracted with ethyl acetate three times, washed by water, brine then the extraction was evaporated, the crude product was purified by chromatography to obtain a yellow solid. The solid was dried in vacuum at 50° C. to give the title compound (130 mg, yield: 30%). LC-MS (ESI) m/z: 465 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (20 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate three times
  6. washwashed by water, brine
  7. extractionthe extraction
  8. customwas evaporated
  9. customthe crude product was purified by chromatography
  10. customto obtain a yellow solid
  11. customThe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-19af3293024941cba5ff8580ce3dd967
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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