Quinoline → HCID 22119901, compound

HRID 1274644Notes

Reaction equation

HRID 1274644 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21](C)([CH3:25])[C:22](O)=O)[C:17]=3[CH:27]=2)[C:3]1=[O:28].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C>[CH:21]([C:18]1[C:17]2[CH:27]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:9])([F:11])[F:10])[N:2]([CH3:1])[C:3]3=[O:28])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1)([CH3:25])[CH3:22]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 22119820HCID 22119820, compound

Product 1

HCID 22119901HCID 22119901, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-α,α-dimethyl-1,2-benzisothiazole-3-acetic acid (2.00 g, 0.00484 mol) and quinoline (20.0 ml) is heated to 140° C. with stirring. After 15 minutes, the mixture is cooled to room temperature, diluted with ethyl acetate, washed sequentially with 2 N hydrochloric acid, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to a yellow solid. The solid is recrystallized from hexanes:methylene chloride to give the title compound as an off-white solid (0.640 g, 35.8%, mp 139-140° C.) which is identified by NMR and IR spectral analyses.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. washwashed sequentially with 2 N hydrochloric acid, saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo to a yellow solid
  5. customThe solid is recrystallized from hexanes

Sources & evidence

ORD record
ord-68827925159e490f876d59d0ca93265d
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

Loading…