Ethanol → HCID 10194514, compound

HRID 1167735Notes

Reaction equation

HRID 1167735 reaction equation
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].Br[C:7]1[CH:8]=[C:9]([CH:30]=[CH:31][N:32]=1)[C:10]([NH:12][C:13]1[S:14][C:15]2[C:21]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:20][CH:19]=[C:18]([O:28][CH3:29])[C:16]=2[N:17]=1)=[O:11]>O1CCOCC1>[CH2:1]([O:3][C:7]1[CH:8]=[C:9]([CH:30]=[CH:31][N:32]=1)[C:10]([NH:12][C:13]1[S:14][C:15]2[C:21]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[CH:20][CH:19]=[C:18]([O:28][CH3:29])[C:16]=2[N:17]=1)=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 229934292-bromo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 10194514HCID 10194514, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 0.52 ml (8.90 mmol) ethanol in 30 ml dioxane at room temperature was added 486 mg (11.1 mmol) sodium hydride (55% dispersion in mineral oil) and the mixture heated at 50° C. for 30 minutes. 1.00 g (2.23 mmol) 2-bromo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide was then added and the mixture heated at 115° C. for 72 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was resuspended in dichloromethane, and washed sequentially with water and saturated brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was resuspended in methanol and concentrated in vacuo to 2 ml, 20 ml ether added, and the resulting crystals were collected by filtration and dried in vacuo to afford 410 mg (44%) 2-ethoxy-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide as a light yellow crystalline solid.

Workup

  1. temperaturethe mixture heated at 115° C. for 72 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. washwashed sequentially with water and saturated brine
  5. dry with materialThe organic phase was then dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. concentrationconcentrated in vacuo to 2 ml, 20 ml ether
  8. additionadded
  9. filtrationthe resulting crystals were collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-039c4b42591a4ee18537d8c884b6aeda
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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