2-[(2-chloro-1-oxo-butyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-trifloromethyl-benzenepropanamide → 1,3-Dihydro-3-ethyl-1-[(2-thiazolyl)-imino]-5-trifluoromethyl-furo[3,4-b]quinoline-9-ol

HRID 1153816Notes

Reaction equation

HRID 1153816 reaction equation
Cl[CH:2]([CH2:27][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:26])[CH2:17][C:18]([NH:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=[O:19])=O>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:27]([CH:2]1[C:3]2=[N:5][C:6]3[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:9]=[CH:8][C:7]=3[C:16]([OH:26])=[C:17]2[C:18](=[N:20][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)[O:19]1)[CH3:28]

Participants

4

Reactant 1

HCID 134230842-[(2-chloro-1-oxo-butyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-trifloromethyl-benzenepropanamide

Product 1

HCID 1784381861,3-Dihydro-3-ethyl-1-[(2-thiazolyl)-imino]-5-trifluoromethyl-furo[3,4-b]quinoline-9-olYield 91.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 g of the product of Step B in 20 ml of tetrahydrofuran and 0.34 g of 4-dimethylamino-pyridine was refluxed for 90 minutes and was evaporated to dryness under reduced pressure. The residue was added to 10 ml of water and was vacuum filtered. The product was dried under reduced pressure at 90° C. to obtain 0.8 g of 1,3-dihydro-3-ethyl-1-[(2-thiazolyl)-imino]-5-trifluoromethyl-furo[3,4-b]quinoline-9-ol melting towards 250°-260° C.

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. additionThe residue was added to 10 ml of water
  3. filtrationfiltered
  4. customThe product was dried under reduced pressure at 90° C.

Sources & evidence

ORD record
ord-8ff283afee954839b416fa04076a4301
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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