N-bromobutanimide → HCID 90409135, compound

HRID 589068Notes

Reaction equation

HRID 589068 reaction equation
[CH3:1][NH:2][C:3]([C:5]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:10]2[C:11](=[O:17])[NH:12][C:13]3=[CH:14][CH:15]=[CH:16][C:8](=[C:9]23)[O:7][CH2:6]1)=[O:4].[Br:24]N1C(=O)CCC1=O>C(#N)C.C(O)(=O)C.C(OCC)(=O)C>[Br:24][C:16]1[C:8]2[O:7][CH2:6][C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)([C:3]([NH:2][CH3:1])=[O:4])[N:10]3[C:11](=[O:17])[NH:12][C:13]([C:9]=23)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 90409674N-methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide

Product 1

HCID 90409135HCID 90409135, compoundYield 51.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide (20 mg, 0.1 mmol) was dissolved in acetonitrile (3 mL) and acetic acid (2 mL), and cooled to 0° C., followed by addition of N-bromosuccinimide (20 mg, 0.1 mmol). The reaction mixture was stirred for 1 h and was then concentrated to give a crude residue. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude 7-bromo-N-methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide (0.020 g, 50%). LCMS calculated for C16H14BrN4O3 (M+H)+: m/z=389.1, 391.1. found: 388.9, 390.9.

Workup

  1. concentrationwas then concentrated
  2. customto give a crude residue
  3. washwashed with saturated aqueous sodium bicarbonate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-af0956e14bfb46a081b590d20b7e5d34
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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