Pyridine → ethyl 3-[4-oxo-7-[3-(trifluoromethyl)-2-pyridinyl]-1H-quinazolin-2-yl]propanoate

HRID 2113609Notes

Reaction equation

HRID 2113609 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=CC=1.[Cl-].[CH2:28]([O:30][C:31](=[O:37])[CH2:32][CH2:33][C:34](Cl)=O)[CH3:29].CC[O-].[Na+]>C1COCC1.CCO>[CH2:28]([O:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]1[N:6]=[C:4]([OH:5])[C:3]2[C:2](=[CH:10][C:9]([C:11]3[C:16]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:8][CH:7]=2)[N:1]=1)[CH3:29]

Participants

7

Reactant 4

HCID 1049PyridineHCID 2723922Sodium ethoxideHCID 220300742-Amino4-(3-trifluoromethyl-pyridin-2-yl)-benzamideHCID 865926183-Chlorocarbonyl-propionic acid ethyl ester chloride

Product 1

HCID 178471181ethyl 3-[4-oxo-7-[3-(trifluoromethyl)-2-pyridinyl]-1H-quinazolin-2-yl]propanoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (0.5 mmol) and pyridine (0.55 mmol) in THF (5 ml), add 3-chlorocarbonyl-propionic acid ethyl ester chloride (0.55 mmol). Stir the mixture for 20 minutes at room temperature, add 20 ml of 21% NaOEt in EtOH, and stir for 30 minutes at 50° C. Concentrate, add water, filter, acidify to pH 6, and collect the precipitate to give 3-[4-hydroxy-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-yl]-propionic acid ethyl ester.

Workup

  1. stirringstir for 30 minutes at 50° C
  2. concentrationConcentrate
  3. additionadd water
  4. filtrationfilter
  5. customcollect the precipitate

Sources & evidence

ORD record
ord-5f7aa16a0399483d825f60aa8a1b5d2f
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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