2-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene-propanamide → HCID 178434920, compound

HRID 1153799Notes

Reaction equation

HRID 1153799 reaction equation
Cl[CH:2]([CH3:28])[C:3]([NH:5][C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:9]=[CH:8][C:7]=1[C:16](=[O:27])[CH2:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[O:19])=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:28][CH:2]1[C:3]2=[N:5][C:6]3[C:11]([C:12]([F:14])([F:15])[F:13])=[CH:10][CH:9]=[CH:8][C:7]=3[C:16]([OH:27])=[C:17]2[C:18](=[N:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[O:19]1

Participants

4

Reactant 1

HCID 134231002-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene-propanamide

Product 1

HCID 178434920HCID 178434920, compoundYield 115.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.60 g of 4-dimethylamino-pyridine were added to a suspension of 4.5 g of the product of Step A in 90 ml of tetrahydrofuran and the mixture was refluxed for four hours and was evaporated to dryness under reduced pressure. The residue was added to 90 ml of water and the mixture was stirred for 30 minutes and was vacuum filtered. The product was washed with water and dried under reduced pressure at 70° C. to obtain 4.50 g of 1,3-dihydro-3-methyl-1-[(2-pyridinyl)-imino]-5-trifluoromethyl-furo[3,4-b]quinoline-9-ol which was crystallized from absolute ethanol.

Workup

  1. temperaturethe mixture was refluxed for four hours
  2. customwas evaporated to dryness under reduced pressure
  3. additionThe residue was added to 90 ml of water
  4. filtrationfiltered
  5. washThe product was washed with water
  6. customdried under reduced pressure at 70° C.

Sources & evidence

ORD record
ord-861f1f95e7444c59824576c41a54c274
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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