Ethanol → HCID 18670166, compound

HRID 1059405Notes

Reaction equation

HRID 1059405 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][C:16]([NH2:18])=[S:17])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.C(O)C.Br.Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)=O.C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C=O>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]1[N:18]=[C:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:7]3[S:6][C:5]4[N:4]=[CH:3][CH:2]=[N:1][C:10]=4[NH:9][C:8]=3[CH:11]=2)[S:17][CH:24]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromideHCID 18670561HCID 18670561, compound

Product 1

HCID 18670166HCID 18670166, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 550 mg of (10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)thioacetamide in a solvent mixture of ethanol (10 ml) with N,N-dimethylformamide (10 ml) was added 560 mg of (2-bromoacetyl)pyridine hydrobromide and the resulting mixture was heated to 60 to 70° C. for 2 hours. Then the reaction mixture was brought back to room temperature and distributed into dichloromethane and an aqueous solution of sodium bicarbonate. After extracting the organic layer, the extract was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crystals thus precipitated were washed successively with ethyl acetate and diethyl ether to thereby give 420 mg of the title compound as yellow crystals.

Workup

  1. customwas brought back to room temperature
  2. extractionAfter extracting the organic layer
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe crystals thus precipitated
  7. washwere washed successively with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-fff897f5e5394777a2cf409c4ef05016
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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