2-(2-chloro-2-phenylacetamido)-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide → HCID 178515160, compound

HRID 1982595Notes

Reaction equation

HRID 1982595 reaction equation
Cl[CH:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[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>CN(C)C1C=CN=CC=1.O1CCCC1>[C:27]1([CH:2]2[C:3]3=[N:5][C:6]4[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:9]=[CH:8][C:7]=4[C:16]([OH:26])=[C:17]3[C:18](=[N:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)[O:19]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 134230822-(2-chloro-2-phenylacetamido)-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

Product 1

HCID 178515160HCID 178515160, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.82 g of 4-dimethylamino-pyridine were added to a solution of 6 g of the product of Step B in 150 ml of tetrahydrofuran and the mixture was stirred at room temperature for 16 hours and was evaporated to dryness under reduced pressure. The residue was extracted with 100 ml of water and 3 ml of hydrochloric acid were added to the aqueous extract which was stirred at room temperature for 15 minutes and was vacuum filtered. The product was washed with water and dried under reduced pressure at 90° C. to obtain 5.34 g of 1,3-dihydro-3-phenyl-1-[(2-thiazolyl)-imino]-5-trifluoromethyl-furo[3,4-b]quinoline-9-ol melting at 270° C. (decomposition).

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. extractionThe residue was extracted with 100 ml of water and 3 ml of hydrochloric acid
  3. additionwere added to the
  4. extractionaqueous extract which
  5. stirringwas stirred at room temperature for 15 minutes
  6. filtrationfiltered
  7. washThe product was washed with water
  8. customdried under reduced pressure at 90° C.

Sources & evidence

ORD record
ord-58ad131e39c04e788e84e2ca46ad6bb0
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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