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

HRID 2385632Notes

Reaction equation

HRID 2385632 reaction equation
BrC1C=CC2C3N=C(N4C(C)=NN(C)C4=O)SC=3CCOC=2C=1.[I:24][C:25]1[CH:46]=[CH:45][C:28]2[C:29]3[N:30]=[C:31](N4C(C)=NN(C)C4=O)[S:32][C:33]=3[CH2:34][CH2:35][O:36][C:27]=2[CH:26]=1.[CH:47]([N:50]1[C:54](=[O:55])[NH:53][C:52]([CH3:56])=[N:51]1)([CH3:49])[CH3:48].BrC1C=CC2C3N=C(N4C(C)=NN(C(C)C)C4=O)SC=3CCOC=2C=1>>[I:24][C:25]1[CH:46]=[CH:45][C:28]2[C:29]3[N:30]=[C:31]([N:53]4[C:52]([CH3:56])=[N:51][N:50]([CH:47]([CH3:49])[CH3:48])[C:54]4=[O:55])[S:32][C:33]=3[CH2:34][CH2:35][O:36][C:27]=2[CH:26]=1

Participants

5

Reactant 4

HCID 670505674-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-oneHCID 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 1363405273-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

Product 1

HCID 670505364-(8-Iodo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one

Procedure

Following a similar procedure for 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 2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one, the mixture of 4-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-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-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one (˜1:1) was isolated as an off-white solid (49 mg). LCMS: RT=5.17 min, [M+H]+=421/423 and 469

Sources & evidence

ORD record
ord-10e549dbb05540979cbd9bb6de22a2ed
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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