2-[(2-chloro-3-methyl-1-oxobutyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene propanamide → HCID 178440487, compound

HRID 231149Notes

Reaction equation

HRID 231149 reaction equation
Cl[CH:2]([CH:28]([CH3:30])[CH3:29])[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.O.CC(C)=O>[CH3:30][CH:28]([CH:2]1[C:3]2=[N:5][C:6]3[C:11]([C:12]([F:14])([F:13])[F:15])=[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)[CH3:29]

Participants

6

Reactant 1

HCID 141405942-[(2-chloro-3-methyl-1-oxobutyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene propanamide

Product 1

HCID 178440487HCID 178440487, compoundYield 84.7%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

10.5 g of the product of Step A and 2.9 g of 4-dimethylamino-pyridine in 100 ml of tetrahydrofuran were refluxed for 7 hours 30 minutes and after cooling, the solvent was eliminated under reduced pressure. The residue was taken up in 100 ml of water and 10 ml of acetone. After separating, washing with water and drying at 70° C. under reduced pressure, 7.8 g of 1,3-dihydro-3-(1-methylethyl)-1-[(2-pyridinyl)-imino]-5-trifluoromethyl furo-[3,4-b]-quinolin-9-ol melting at 178°-180° C. were obtained.

Workup

  1. temperatureafter cooling
  2. customAfter separating
  3. washwashing with water
  4. customdrying at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-3ad4a52355b24c6da1d29d6722e52a4e
Source dataset
uspto-grants-1989_07
Patent number
US04845105

Reaction notes

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