N-bromobutanimide → HCID 89541876, compound

HRID 1509235Notes

Reaction equation

HRID 1509235 reaction equation
[C:1]1([C:7]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)=[N:18][C:10]3[O:11][CH2:12][C:13]4[N:14]([CH:15]=[N:16][N:17]=4)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:38]N1C(=O)CCC1=O>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[C:33]([O:32][C:31](=[O:37])[NH:30][C:26]1([C:23]2[CH:24]=[CH:25][C:20]([C:19]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][C:9]4[N:14]5[C:15]([Br:38])=[N:16][N:17]=[C:13]5[CH2:12][O:11][C:10]=4[N:18]=3)=[CH:21][CH:22]=2)[CH2:27][CH2:28][CH2:29]1)([CH3:34])([CH3:36])[CH3:35]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67255018HCID 67255018, compound

Product 1

HCID 89541876HCID 89541876, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 1-(4-(8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutylcarbamate (200 mg, 0.404 mmol) and 1-bromopyrrolidine-2,5-dione (114.9275 mg, 0.646 mmol) in DCM (12 ml) and CCl4 (18 ml) was heating at 50 degree for 24 h. The mixture was concentrated and the residue was partitioned between ethyl acetate (40 ml) and water (40 ml). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (30 ml). The combined organic phase was washed with water (50 ml) brine (30 ml) and concentrated to give product 159 mg. 1H NMR (500 MHz, CDCl3): 8.55 (s, 1H), 7.22-7.35 (m, 9H), 5.58 (s, 2H), 5.1 (br, 1H), 2.4-2.5 (m, 4H), 2.01-2.11 (m, 1H), 1.79-1.89 (m, 1H), 1.24-1.43 (br, 9H).

Workup

  1. temperaturewas heating at 50 degree for 24 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate (40 ml) and water (40 ml)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (30 ml)
  6. washThe combined organic phase was washed with water (50 ml) brine (30 ml)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e128ca027ce14f0fa913b650584a4b85
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

Loading…