Ammonia methanol → 9-Bromo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxamide

HRID 1799896Notes

Reaction equation

HRID 1799896 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[N:14]([N:15]=1)[C:13]1[CH:16]=[C:17]([Br:20])[CH:18]=[CH:19][C:12]=1[O:11][CH2:10][CH2:9]2)=O)C.[NH3:21].CO>>[Br:20][C:17]1[CH:18]=[CH:19][C:12]2[O:11][CH2:10][CH2:9][C:8]3[N:14]([N:15]=[C:6]([C:4]([NH2:21])=[O:3])[CH:7]=3)[C:13]=2[CH:16]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 58204733Ethyl 9-bromo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 582043309-Bromo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxamideYield 80%

Procedure

9-Bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid ethyl ester (1.51 g, 4.48 mmol) in 2M ammonia/methanol solution (70 mL) was heated in a pressure bomb at approximately 120° C. (external temperature) for 30 h, then allowed to cool. The mixture was filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 50 to 100% ethyl acetate in cyclohexane) to give 9-Bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid amide as a pale yellow solid (1.11 g, 80%). LCMS: RT=4.00 min, M+H+=308/310, [M+Na]+=330/332.

Workup

  1. temperatureto cool
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4967c08e73da4acbb1ec507aa02862c8
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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