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

HRID 723523Notes

Reaction equation

HRID 723523 reaction equation
[SH:1][CH2:2][C:3](OCC)=[O:4].[H-].[Na+].[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:4]=[C:3]1[CH2:2][S:1][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-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-mercaptoacetate (1.473 ml) in DMF (48 ml) was ice-cooled and treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 hour methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623-4633) was added and the mixture stirred for 16 hours at room temperature. The solution was diluted with EtOAc (1 liter), washed with water (3×300 ml), dried and evaporated to about 10 ml. The white solid was filtered off and washed with a little EtOAc to the ester (0.95 g).

Workup

  1. temperaturecooled
  2. addition61, 1996, 4623-4633) was added
  3. washwashed with water (3×300 ml)
  4. customdried
  5. customevaporated to about 10 ml
  6. filtrationThe white solid was filtered off
  7. washwashed with a little EtOAc to the ester (0.95 g)

Sources & evidence

ORD record
ord-e12f0e6080b7444db2eb73ff7b50675d
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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