3-{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-8-yl}-azetidine-1-carboxylic acid tert-butyl ester → 3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:38]=[CH:37][C:15]3[C:16]4[C:20]([CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)=[CH:19][N:18]([C:24]2[N:25]([C:29]3[CH:34]=CC(F)=C[C:30]=3F)[N:26]=[CH:27][N:28]=2)[N:17]=4)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC1C=CC2C3C(CCOC=2C=1)=CN(C1N(C(C)C)N=CN=1)N=3>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[CH:38]=[CH:37][C:15]3[C:16]4[C:20]([CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)=[CH:19][N:18]([C:24]2[N:25]([CH:29]([CH3:30])[CH3:34])[N:26]=[CH:27][N:28]=2)[N:17]=4)[CH2:11]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester was prepared similarly to 3-{2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-8-yl}-azetidine-1-carboxylic acid tert-butyl ester from 8-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene and 3-azetidine-1-carboxylic acid tert-butyl ester zinc iodide. LCMS: RT=4.85 min, M+H+=451 (40%), M+H+−OtBu=395 (100%), M+H+−Boc=351 (10%).
Sources & evidence
- ORD record
- ord-48ec280cfc694f7299437b79de87f0f0
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586574B2
Reaction notes
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