Triethylamine → 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one

HRID 734216Notes

Reaction equation

HRID 734216 reaction equation
[O:1]=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12](O)=[O:13])=[N:11][C:4]=2[NH:3]1.C(N(CC)CC)C.ClC(OCC(C)C)=O>C1COCC1>[OH:13][CH2:12][C:10]1[CH:9]=[CH:8][C:5]2[S:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=2[N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid

Product 1

HCID 116080936-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-oneYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (500 mg) in THF (24 mL) with triethylamine (0.396 mL) was cooled to −10° C. and isobutyl chloroformate (0.339 ml) was added. After 20 minutes the suspension was filtered through kieselguhr into an ice-cooled solution of sodium borohydride (272 mg) in water (8 mL), the mixture stirred 30 minutes and the pH reduced to 7 with dilute HCl. The solvent was evaporated and the residue triturated under water. The product was filtered and dried under vacuum to give a white solid (346 mg); LC/MS (APCI−) m/z 195 ([M−H]−, 50%), 165(100%).

Workup

  1. filtrationAfter 20 minutes the suspension was filtered through kieselguhr into an ice-
  2. temperaturecooled solution of sodium borohydride (272 mg) in water (8 mL)
  3. customThe solvent was evaporated
  4. customthe residue triturated under water
  5. filtrationThe product was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3a3b0f6dc0714e46acc9759987ba9945
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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