Water → HCID 18670477, compound

HRID 1059359Notes

Reaction equation

HRID 1059359 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22][C:23]([C:25]5[CH:26]=[N:27][O:28][C:29]=5[CH3:30])=[O:24])[CH2:18][CH2:17]4)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.COC(OC)N(C)C.O.C(OCC)(=O)C>O1CCCC1>[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:24])[CH:25]([C:26]#[N:27])[C:29](=[O:28])[CH3:30])[CH2:18][CH2:17]4)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 18670253HCID 18670253, compound

Product 1

HCID 18670477HCID 18670477, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 10 ml of a solution of 500 mg of N-[1-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-piperidin-4-yl]-5-methyl-1,2-oxazole-4-carboxamide in tetrahydrofuran was added 400 μl of N,N-dimethylformamide dimethyl acetal and the resulting mixture was heated under reflux for 4 hours. After distributing into water and ethyl acetate, the aqueous layer was extracted and washed with diethyl ether. After distilling off the organic solvent contained therein under reduced pressure, the residue was acidified with dilute hydrochloric acid and purified by high-porous gel chromatography (CHP20P, 75-150μ; manufactured by Mitsubishi Chemical Industries) (eluted with methanol/water) to thereby give 110 mg of the title compound as pale yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionthe aqueous layer was extracted
  4. washwashed with diethyl ether
  5. distillationAfter distilling off the organic solvent
  6. custompurified by high-porous gel chromatography (CHP20P, 75-150μ; manufactured by Mitsubishi Chemical Industries) (eluted with methanol/water)

Sources & evidence

ORD record
ord-1256f286c36b4a06baa3474c99bb9de4
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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