6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one → HCID 67223394, compound

HRID 1801474Notes

Reaction equation

HRID 1801474 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[C:13]([Si:17]([CH3:25])([CH3:24])[O:18][CH2:19][CH2:20][C@@H:21]1[CH2:23][O:22]1)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.CO>[C:13]([Si:17]([CH3:25])([CH3:24])[O:18][CH2:19][CH2:20][C@@H:21]([OH:22])[CH2:23][NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1)([CH3:14])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 11217932HCID 11217932, compound

Product 1

HCID 67223394HCID 67223394, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 6.49 g, 39.5 mmol) and tert-butyl-dimethyl-[(R)-2-oxiranyl-ethoxy]-silane (first eluting compound of step P.i of Preparation P; 8.0 g, 39.5 mmol) in EtOH/H2O 9-1 (240 mL) was heated at 80° C. for 2 days. The mixture was concentrated under reduced pressure. Residual starting aniline could be removed by addition of Et2O/MeOH followed by filtration. The filtrate containing the product was concentrated under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4) to afford the title intermediate as a brown oil (5.82 g, 40% yield).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customcould be removed by addition of Et2O/MeOH
  3. filtrationfollowed by filtration
  4. additionThe filtrate containing the product
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4)

Sources & evidence

ORD record
ord-c6c00475f8654431a21cd2176ff033d8
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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