Triphosgene → 4-ethyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one

HRID 589061Notes

Reaction equation

HRID 589061 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]([C:15]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[NH:20][C:19]2=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=[C:18]2[O:17][CH2:16]1)[CH3:14]>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH2:13]([C:15]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[N:20]2[C:2](=[O:4])[NH:25][C:21]3=[CH:22][CH:23]=[CH:24][C:18](=[C:19]23)[O:17][CH2:16]1)[CH3:14]

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 904099193-ethyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine

Product 1

HCID 904092814-ethyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-oneYield 213.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

Triphosgene (40 mg, 0.1 mmol) was added to a solution of 3-ethyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine (80 mg, 0.3 mmol) in tetrahydrofuran (5 mL) and N,N-diisopropylethylamine (0.1 mL). The reaction was stirred at room temperature for 1 h and was then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude 4-ethyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (0.060 g. 60%). LCMS calculated for C16H16N3O2 (M+H)+: m/z=282.1. found: 282.0.

Workup

  1. customwas then partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3780f63746fb47be8050cb5ae6e08b0a
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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