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 1982612Notes

Reaction equation

HRID 1982612 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-ol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 f 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 vaccum 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. customThe product was dried under reduced pressure at 90° C.

Sources & evidence

ORD record
ord-64684166c38b4fd890fee2f280475c49
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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