N-bromobutanimide → HCID 67364381, compound

HRID 1182716Notes

Reaction equation

HRID 1182716 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14]([N:16]1[CH2:25][C:24]2[N:20]([CH:21]=[N:22][N:23]=2)[C:19]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:18]=2[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>O1CCCC1>[C:9]([O:13][C:14]([N:16]1[CH2:25][C:24]2[N:20]([C:21]([Br:1])=[N:22][N:23]=2)[C:19]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:18]=2[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 673654941,1-Dimethylethyl 8-chloro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-5(6H)-carboxylate

Product 1

HCID 67364381HCID 67364381, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Bromosuccinimide (4.50 g, 24.0 mmol) was added to 8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester (7.00 g, 21.8 mmol) in tetrahydrofuran (140 ml). The mixture was stirred in boiling tetrahydrofuran for 2 hours. The solvent was removed in vacuo and the residue was purified by chromatography (50 g silica gel, heptane: ethylacetate 1:9 to 1:0) to yield 7.39 g (85%) 1-bromo-8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester as white solid. MS m/e: 401 (M+H+).

Workup

  1. customfor 2 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by chromatography (50 g silica gel, heptane: ethylacetate 1:9 to 1:0)

Sources & evidence

ORD record
ord-b1fdffb1790a4a76999b951b6d7b47b4
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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