4-Chlorobenzoyl chloride → HCID 67391610, compound

HRID 910629Notes

Reaction equation

HRID 910629 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[NH:9][C:10](=[O:29])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:28])[N:19]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1.[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>N1C=CC=CC=1>[ClH:30].[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=2[NH:9][C:10](=[O:29])[C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:18](=[O:28])[N:19]([CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])[CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)=[O:36])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 57584187HCID 57584187, compound

Product 1

HCID 67391610HCID 67391610, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(2-amino-6-hydroxyphenyl)-4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzamide (276 mg) was dissolved in pyridine (6 mL), and with cooling with ice, 4-chlorobenzoyl chloride (99 μL) was added, followed by stirring overnight at room temperature. The reaction solution was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=100:0:0 to 95:5:0.5). The purified product (250 mg) was dissolved in ethyl acetate, and 4 M hydrochloric acid/ethyl acetate solution (129 μL) was added, followed by stirring at room temperature for 1 hour. The precipitate formed was collected by filtration and dried at room temperature under reduced pressure to obtain 4-chloro-N-{2-[(4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoyl)amino]-3-hydroxyphenyl}benzamide hydrochloride (157 mg) as a white solid.

Workup

  1. additionwas added
  2. customThe reaction solution was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=100:0:0 to 95:5:0.5)
  4. dissolutionThe purified product (250 mg) was dissolved in ethyl acetate
  5. addition4 M hydrochloric acid/ethyl acetate solution (129 μL) was added
  6. stirringby stirring at room temperature for 1 hour
  7. customThe precipitate formed
  8. filtrationwas collected by filtration
  9. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-99cc3b6bbde54cf5a7757c5868c76b93
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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