N-bromobutanimide → HCID 86299111, compound

HRID 589037Notes

Reaction equation

HRID 589037 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:12]4[C:23](=[O:25])[NH:24][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[CH:5][CH:4]=[N:3]1.[Br:26]N1C(=O)CCC1=O>C1COCC1>[Br:26][C:9]1[CH:8]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[C:16]2[O:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:12]3[C:23](=[O:25])[NH:24][C:10]=1[C:11]=23

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90409533HCID 90409533, compound

Product 1

HCID 86299111HCID 86299111, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(1-methyl-1H-pyrazol-5-yl)-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (32 mg, 0.096 mmol) in THF (0.7 mL) was added N-bromosuccinimide (19 mg, 0.10 mmol). The solution was stirred at room temperature for 1 h and then concentrated under reduced pressure. Purification on silica gel using EtOAc/hexane gave the title compound, 24 mg. LCMS calc. for C19H16BrN4O2 (M+H)+: m/z=411.0, 413.0. found: 411.1, 413.1. 1H NMR (300 MHz, DMSO-d6): d 7.40 (s, 1H); 7.31 (m, 3H); 7.13 (m, 2H); 7.08 (s, 1H); 6.30 (s, 1H); 5.50 (s, 1H); 4.59 (m, 1H); 4.41 (m, 1H); 3.60 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification on silica gel

Sources & evidence

ORD record
ord-189b60007c7441dc8cdbc96c525fe6d2
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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