Acetic Acid → HCID 90410414, compound

HRID 589050Notes

Reaction equation

HRID 589050 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH:7]1[N:12]2[C:13](=[O:19])[NH:14][C:15]3=[CH:16][CH:17]=[CH:18][C:10](=[C:11]23)[O:9][CH2:8]1.C(O)(=O)C.[Br:24]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:24][C:18]1[C:10]2[O:9][CH2:8][CH:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][NH:1]3)[N:12]3[C:13](=[O:19])[NH:14][C:15]([C:11]=23)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 90409483HCID 90409483, compound

Product 1

HCID 90410414HCID 90410414, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 4-piperidin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (0.20 g, 0.77 mmol) of Step 1 was dissolved in acetic acid (10.0 mL, 176 mmol) at room temperature and N-bromosuccinimide (0.14 g, 0.77 mmol) was slowly added. The reaction was stirred for 2 h and was concentrated in vacuo to give a residue. The residue was dissolved in ethyl acetate, washed with aqueous potassium carbonate, washed with brine, dried over magnesium sulfate, and concentrated to give 7-bromo-4-piperidin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as a dark oil (0.22 g, 85%). LCMS calculated for C14H17BrN3O2 (M+H)+: m/z=338.0, 340.0. found: 338.0, 340.0.

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give a residue
  3. washwashed with aqueous potassium carbonate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-36c9085b930b4ec999f32fc9767353e2
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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