2-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide → HCID 178494648, compound

HRID 1982593Notes

Reaction equation

HRID 1982593 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:8]=1[C:17](=[O:27])[CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[CH:25][N:26]=1)=[O:20])=O>CN(C)C1C=CN=CC=1.O1CCCC1>[OH:27][C:17]1[C:8]2[C:7](=[C:12]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:10][CH:9]=2)[N:6]=[C:4]([CH2:3][O:2][CH3:1])[C:18]=1[C:19]([NH:21][C:22]1[S:23][CH:24]=[CH:25][N:26]=1)=[O:20]

Participants

4

Reactant 1

HCID 133813462-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

Product 1

HCID 178494648HCID 178494648, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

5.03 g of 4-dimethylamino-pyridine were added to a solution of 16.5 g of the product of Step B in 205 ml of tetrahydrofuran and the mixture was stirred at 20° C. for 41/2 hours. The tetrahydrofuran was distilled off under reduced pressure at 40° C. and the dry residue wsa taken up in 500 ml of water. 42 ml of N hydrochloric acid were added to the mixture and the suspension was stirred at 20° C. for 30 minutes and was vacuum filtered. The product was washed with water, dried under reduced pressure at 70° C. and was crystallized from 310 ml of dioxane. The mixture was vacuum filtered at 15° C. and the product was washed with 30 ml of dioxane and dried under reduced pressure at 70° C. to obtain 13.3 g of 4-hydroxy-2-methoxymethyl-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 260° C.

Workup

  1. distillationThe tetrahydrofuran was distilled off under reduced pressure at 40° C.
  2. addition42 ml of N hydrochloric acid were added to the mixture
  3. stirringthe suspension was stirred at 20° C. for 30 minutes
  4. filtrationfiltered
  5. washThe product was washed with water
  6. customdried under reduced pressure at 70° C.
  7. customwas crystallized from 310 ml of dioxane
  8. filtrationfiltered at 15° C.
  9. washthe product was washed with 30 ml of dioxane
  10. customdried under reduced pressure at 70° C.

Sources & evidence

ORD record
ord-d3adca27bd8e458a9bcdb7dbf8582fc9
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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