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

HRID 1435852Notes

Reaction equation

HRID 1435852 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 (0.4.mL) was cooled to −10° C. and isobutyl chloroformate (0.339 mL) added. After 20 minutes the suspension was filtered through celite 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). MS (APCl−) m/e 195 ([M−H]−, 50%), 165(100%).

Workup

  1. filtrationAfter 20 minutes the suspension was filtered through celite 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-19bbf04581de4e5f96c172ef36d2005e
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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