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

HRID 1271696Notes

Reaction equation

HRID 1271696 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 16 hours at room temp. 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 give a solid (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

Sources & evidence

ORD record
ord-4d1ec86b0b8e41549a256d82d080f8ce
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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