Benzaldehyde → HCID 178422688, compound

HRID 2061132Notes

Reaction equation

HRID 2061132 reaction equation
[NH2:1][C:2]1[C:3]([F:27])=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][C:6]1[C:7](=[O:23])[O:8][C:9]2[CH:16]=[C:15]([O:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)[CH:14]=[CH:13][C:10]=2[C:11]=1[CH3:12].[CH:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO>[F:27][C:3]1[C:2](/[N:1]=[CH:28]\[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:26][CH:25]=[CH:24][C:4]=1[CH2:5][C:6]1[C:7](=[O:23])[O:8][C:9]2[CH:16]=[C:15]([O:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)[CH:14]=[CH:13][C:10]=2[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 59139203HCID 59139203, compound

Product 1

HCID 178422688HCID 178422688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (4.0 mL) was added to 3-(3-amino-2-fluorobenzyl)-4-methyl-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran (compound 1h-3-4) (200 mg), and benzaldehyde (0.053 mL) was added to the resultant suspension while stirring at room temperature. The suspension was heated under reflux for 3 hours. The reaction solution was then cooled to room temperature, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel chromatography (amino gel) (dichloromethane) to yield the title compound (233 mg).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction solution was then cooled to room temperature
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resultant residue was purified by silica gel chromatography (amino gel) (dichloromethane)

Sources & evidence

ORD record
ord-e6474c60eab244db84462e782883de3a
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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