Acetic Acid → 9-Bromo-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 1799871Notes

Reaction equation

HRID 1799871 reaction equation
C[N:2](C)/[C:3](=[N:5]/[C:6]([C:8]1[N:17]=[C:16]2[N:10]([CH2:11][CH2:12][O:13][C:14]3[CH:21]=[C:20]([Br:22])[CH:19]=[CH:18][C:15]=32)[CH:9]=1)=O)/[CH3:4].C(O)(=O)C.Cl.[CH:29]([NH:32]N)([CH3:31])[CH3:30]>>[Br:22][C:20]1[CH:19]=[CH:18][C:15]2[C:16]3[N:10]([CH2:11][CH2:12][O:13][C:14]=2[CH:21]=1)[CH:9]=[C:8]([C:6]1[N:32]([CH:29]([CH3:31])[CH3:30])[N:2]=[C:3]([CH3:4])[N:5]=1)[N:17]=3

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 855731-Isopropylhydrazine hydrochlorideHCID 178464914HCID 178464914, compound

Product 1

HCID 582043229-Bromo-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineYield 83.8%

Conditions

Temperature
95 °C

Procedure

To a solution of 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid [1-dimethylamino-eth-(E)-ylidene]-amide (0.340 g, 0.000901 mol) in acetic acid (3.0 mL, 0.053 mol) was added isopropylhydrazine hydrochloride (0.1196 g, 0.001082 mol). The reaction was heated to 95° C. for 3 h. The acetic acid was removed in vacuo and the product was loaded as a solid onto silica and purified by flash chromatography (0-10% MeOH in DCM) to give 8-Bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene (293 mg) as an orange solid. MS (ESI+) 388.1/390.1

Workup

  1. customThe acetic acid was removed in vacuo
  2. custompurified by flash chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-1d912c06109e49739b9fc67c5dec3c5f
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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