Triphosgene → HCID 90408783, compound

HRID 589057Notes

Reaction equation

HRID 589057 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][C:14]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[NH:19][C:18]2=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=[C:17]2[O:16][CH2:15]1>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH3:13][C:14]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:19]2[C:2](=[O:4])[NH:24][C:20]3=[CH:21][CH:22]=[CH:23][C:17](=[C:18]23)[O:16][CH2:15]1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 90408833HCID 90408833, compound

Product 1

HCID 90408783HCID 90408783, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

Triphosgene (40 mg, 0.1 mmol) was added to the solution of 3-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine (90 mg, 0.4 mmol) in tetrahydrofuran (10 mL) and N,N-diisopropylethylamine (100 μL) at room temperature. The reaction was stirred for 1 h and was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude 4-methyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as a semisolid (0.10 g. 90%). LCMS calculated for C15H14N3O2 (M+H)+: m/z=268.1. found: 268.0.

Workup

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

Sources & evidence

ORD record
ord-b20c8d3827ee469e91249c77b394e63d
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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