6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde

HRID 2233337Notes

Reaction equation

HRID 2233337 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:7][CH2:8][C:9](=[O:13])[NH:10][C:11]=2[N:12]=1>C(Cl)Cl.C1COCC1.O=[Mn]=O>[O:13]=[C:9]1[CH2:8][S:7][C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[N:12][C:11]=2[NH:10]1

Participants

5

Reactant 1

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

Product 1

HCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeYield 55.2%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-hydroxymethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine (330 mg, 1.68 mmole) in CH2Cl2 (30 mL) and THF (30 mL) was treated with MnO2 (730 mg, 8.40 mmole), and the mixture was stirred at RT. Additional MnO2 was added after 1 hr (730 mg, 8.40 mmole) and after 16 hr (300 mg, 3.45 mmole). After a total of 20 hr the mixture was filtered through kieselguhr and the filtrate was concentrated to dryness. The reside was triturated with 1:1 EtOAc/hexanes, collected, and dried to afford the title compound (180 mg, 55%) as a solid: MS (APCI−) m/e 195 (M−H)−.

Workup

  1. filtrationAfter a total of 20 hr the mixture was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe reside was triturated with 1:1 EtOAc/hexanes
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-4908b57416094227881ef13ed88aeb56
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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