2-Propanamine, hydrochloride (1:1) → 8-Bromo-2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 2385603Notes

Reaction equation

[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[N:7]=[C:8]([C:14]4O[CH:16]=[N:17][N:18]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.Cl.[CH:22]([NH2:25])([CH3:24])[CH3:23]>N1C=CC=CC=1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:25]([CH:22]([CH3:24])[CH3:23])[CH:16]=[N:17][N:18]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 8-bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (4.38 g, 12.51 mmol) in pyridine (12 mL) was added isopropylamine hydrochloride (1.38 g, 12.51 mmol). The reaction mixture was heated at 160° C. for 30 minutes using microwave irradiation before being concentrated in vacuo. The residue was taken up into DCM then washed with 1M HCl then brine before being dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, gradient 0-3% methanol in DCM then further purified, gradient 0-4% MeOH in EtOAc) to yield the title compound as an orange solid (1.97 g, 40%). LCMS: RT=4.67 min, M+H+=391/393.

Workup

custommicrowave irradiation
concentrationbefore being concentrated in vacuo
washthen washed with 1M HCl
dry with materialbrine before being dried (Na2SO4)
concentrationconcentrated in vacuo
customThe resultant residue was purified by flash chromatography (SiO2, gradient 0-3% methanol in DCM
customthen further purified

Sources & evidence

ORD record: ord-8edbd0d86c254f69879d6ea6655ead58
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263633B2

Reaction notes

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