6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → HCID 67349971, compound

HRID 1916325Notes

Reaction equation

HRID 1916325 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][CH2:8][CH2:9][C@H:10]1[CH2:12][O:11]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>CC#N>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][CH2:8][CH2:9][C@H:10]([OH:11])[CH2:12][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 11528620HCID 11528620, compound

Product 1

HCID 67349971HCID 67349971, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (S)-tert-butyl-dimethyl-(3-oxiranyl-propoxy)-silane (28.3 g, prepared according to Org. Lett. (2005), 7, 3997) and 6-amino-4H-benzo[1,4]thiazin-3-one (23.6 g) in MeCN (390 mL) was treated with LiClO4 (41.8 g) and heated at 60° C. for 4 h. The volatiles were removed under reduced pressure and the residue partitioned between EA and brine. The org. phase was dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 1:1, EA) to give the desired intermediate as a yellowish foam (8.4 g; 16% yield).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue partitioned between EA and brine
  3. dry with materialphase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by CC (Hept/EA 1:1, EA)

Sources & evidence

ORD record
ord-8c78522101974a2db64b0258c4585f91
Source dataset
uspto-grants-2013_12
Patent number
US08618092B2

Reaction notes

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