Potassium Carbonate → 4-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-5-isopropyl-2-methyl-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1190302Notes

Reaction equation

HRID 1190302 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[N:7]=[C:8](N4C(C)=NN(C)C4=O)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.IC1C=CC2C3N=C(N4C(C)=NN(C)C4=O)SC=3CCOC=2C=1.[CH:47]([C:50]1[NH:51][C:52](=[O:56])[N:53]([CH3:55])[N:54]=1)([CH3:49])[CH3:48].C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[N:7]=[C:8]([N:51]4[C:50]([CH:47]([CH3:49])[CH3:48])=[N:54][N:53]([CH3:55])[C:52]4=[O:56])[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 670505734-(8-Iodo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2,5-dimethyl-2,4-dihydro-[1,2,4]triazol-3-oneHCID 670505884-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2,5-dimethyl-2,4-dihydro-[1,2,4]triazol-3-oneHCID 1360579243-isopropyl-1-methyl-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 582039344-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-5-isopropyl-2-methyl-2,4-dihydro-[1,2,4]triazol-3-one

Procedure

The title compound was prepared by a similar method to the mixture of 4-(8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2,5-dimethyl-2,4-dihydro-[1,2,4]triazol-3-one and 4-(8-iodo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2,5-dimethyl-2,4-dihydro-[1,2,4]triazol-3-one using 5-isopropyl-2-methyl-2,4-dihydro-[1,2,4]triazol-3-one and potassium carbonate. 4-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-5-isopropyl-2-methyl-2,4-dihydro-[1,2,4]triazol-3-one was isolated as a yellow solid (11 mg, 17%). LCMS: RT=5.19 min, [M+H]+=421/423

Sources & evidence

ORD record
ord-5fd9fdd0ab984cbebd8fbaac03e38705
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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