6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → HCID 66736420, compound

HRID 1640515Notes

Reaction equation

HRID 1640515 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:13][O:12]1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:17]=[CH:18][C:19]2[S:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=1>CCO.O>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][NH:15][C:16]1[CH:17]=[CH:18][C:19]2[S:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 45091966Carbamic acid, (3-oxiranylpropyl)-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 66736420HCID 66736420, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of ((rac)-3-oxiranyl-propyl)-carbamic acid tert-butyl ester (1.08 g, 5.34 mmol) and 6-amino-4H-benzo[1,4]thiazin-3-one (1.01 g, 5.61 mmol) in 9:1 EtOH/H2O (20 mL) was heated at 70° C. overnight. After cooling the mixture was concentrated in vacuo and chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4) to afford the title intermediate as beige foam (767 mg, 38% yield).

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationwas concentrated in vacuo
  3. customchromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4)

Sources & evidence

ORD record
ord-a3fcab610bf0406b8f2ccf89eab9f990
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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