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

HRID 1992504Notes

Reaction equation

HRID 1992504 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 (APCl−) 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-088acd63e9be4081a3342c37e7fd5b4c
Source dataset
uspto-grants-2010_01
Patent number
US07648984B2

Reaction notes

Loading…