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

HRID 2233336Notes

Reaction equation

HRID 2233336 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.[BH4-].[Na+].Cl>C1COCC1.O>[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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 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 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (500 mg, 2.38 mmole) and triethylamine (0.396 mL, 2.84 mmole) in THF (24 mL) was cooled to −10° C. and isobutyl chloroformate (0.339 mL, 2.61 mmole) was added. After 20 min the suspension was filtered through kieselguhr into an ice-cooled solution of sodium borohydride (272 mg, 7.19 mmole) in water (8 mL). The mixture was stirred for 30 min, then the pH was adjusted to 7 with dilute HCl. The solvent was evaporated and the residue was triturated with water. The solid was collected and dried under vacuum to give the title compound (346 mg, 74%) as a white solid: MS (APCI−) m/e 197 (M−H)−.

Workup

  1. filtrationAfter 20 min the suspension was filtered through kieselguhr into an ice-
  2. customThe solvent was evaporated
  3. customthe residue was triturated with water
  4. customThe solid was collected
  5. customdried under vacuum

Sources & evidence

ORD record
ord-20cfe4e4ecc34bd0b7ac0237af875513
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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