Ethyl Thioglycolate → Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

HRID 2233334Notes

Reaction equation

HRID 2233334 reaction equation
[H-].[Na+].[C:3](OCC)(=[O:6])[CH2:4][SH:5].[NH2:10][C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:12]=1Br>CN(C=O)C.CCOC(C)=O>[O:6]=[C:3]1[CH2:4][S:5][C:12]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[N:16][C:11]=2[NH:10]1

Participants

6

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 10704661Methyl 6-amino-5-bromopicolinate

Product 1

HCID 21873660Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylateYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 540 mg, 13.5 mmole) was added to a solution of ethyl thioglycolate (1.473 mL, 13.43 mmole) in DMF (48 mL) at 0° C. After 1 hr, methyl 6-amino-5-bromopyridine-2-carboxylate (3 g, 13 mmole; prepared by the method of Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623-4633) was added and the mixture was stirred at RT. After 16 hr, the solution was diluted with EtOAc (1 L), washed with water (3×300 mL), dried and concentrated to about 10 mL. The white solid was collected and washed with a little EtOAc to give the title compound (950 mg, 33%): MS (APCI−) m/e 223 (M−H)−.

Workup

  1. customprepared by the method of Kelly, T
  2. addition1996, 61, 4623-4633) was added
  3. waitAfter 16 hr
  4. washwashed with water (3×300 mL)
  5. customdried
  6. concentrationconcentrated to about 10 mL
  7. customThe white solid was collected
  8. washwashed with a little EtOAc

Sources & evidence

ORD record
ord-6243fdc973e746cbbfea42c543ba6e3d
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

Loading…