6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → HCID 67222622, compound

HRID 1259839Notes

Reaction equation

HRID 1259839 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@@H:11]1[CH2:13][O:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]2[S:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=2[CH:25]=1>CCO.O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH2:9][CH2:10][C@@H:11]([OH:12])[CH2:13][NH:14][C:15]1[CH:16]=[CH:17][C:18]2[S:23][CH2:22][C:21](=[O:24])[NH:20][C:19]=2[CH:25]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 11217932HCID 11217932, compound

Product 1

HCID 67222622HCID 67222622, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of (2R)-2-[2-[[tert-butyldimethylsilyl]oxy]ethyl]-oxirane (12.0 g; prepared according to WO 2007/144423) and 6-amino-4H-benzo[1,4]thiazin-3-one (10.7 g; commercial) in EtOH/water (9:1) was heated to 80° C. for 2 days. The solvents were removed under reduced pressure and the residue was triturated in ether/MeOH and filtered. The filtrate was evaporated under reduced pressure, affording a brown oil (18.8 g; 83% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was triturated in ether/MeOH
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customaffording a brown oil (18.8 g; 83% yield)

Sources & evidence

ORD record
ord-01e50a8d86a04547ac8a5abcd7bbfbe4
Source dataset
uspto-grants-2013_06
Patent number
US08466168B2

Reaction notes

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