Pyridine → HCID 67390944, compound

HRID 910852Notes

Reaction equation

HRID 910852 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[NH:14])[NH:12][OH:13])=[CH:7][C:6]=1[Cl:15].[C:21](Cl)(=[O:23])[CH3:22].N1C=CC=[CH:27][CH:26]=1>Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:2]([NH:1][C:21](=[O:23])[CH3:22])=[C:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[N:14]=[C:26]([CH3:27])[O:13][N:12]=3)=[CH:7][C:6]=2[Cl:15])[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 178513351HCID 178513351, compound

Product 1

HCID 67390944HCID 67390944, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The subtitle compound was prepared using the product from step i) (0.94 g) which was dissolved in pyridine (10 ml) and treated with acetyl chloride (0.22 ml) at 0 C. This was then allowed to warm to room temperature. The mixture was heated at reflux for 3 hours, diluted with 2M HCl, extracted with ethyl acetate, dried and concentrated under reduced pressure to an oil. The residue was purified by chromatography on silica eluting with diethyl ether/isohexane 3:1, yield 0.50 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure to an oil
  6. customThe residue was purified by chromatography on silica eluting with diethyl ether/isohexane 3:1, yield 0.50 g

Sources & evidence

ORD record
ord-03b681656ac44b19a07efd2264ea86bf
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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