Pyridine → HCID 21936632, compound

HRID 1241716Notes

Reaction equation

HRID 1241716 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[CH:11]=[C:10]([CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:9]2=[O:27])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>>[C:34]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[CH:11]=[C:10]([CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:9]2=[O:27])[CH:5]=[CH:6][CH:7]=1)(=[O:36])[CH3:35]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21936625HCID 21936625, compound

Product 1

HCID 21936632HCID 21936632, compoundYield 82%

Procedure

1-(3-Aminophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (100 mg, 0.28 mmol; prepared in Synthetic Example 7) was heated in acetic anhydride (0.5 ml) and pyridine (0.5 ml) at 100° C. for 20 min, concentrated, neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with chloroform. The extract was treated according to conventional techniques. Recrystallization from DMF yielded 1-(3-acetylaminophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (91.3 mg, 82%; mp 200–202° C./DMF).

Workup

  1. concentrationconcentrated
  2. extractionextracted with chloroform
  3. additionThe extract was treated
  4. customRecrystallization from DMF

Sources & evidence

ORD record
ord-dbc2d1a5ca5540c6ad3673664d379517
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

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