8-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene → 3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 2044297Notes

Reaction equation

HRID 2044297 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]4C([CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)=CN(C2N(C3C=CC(F)=CC=3F)N=CN=2)[N:17]=4)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC1C=CC2C3[N:48](CCOC=2C=1)[CH:47]=[C:46]([C:52]1[N:53]([CH:57]([CH3:59])[CH3:58])[N:54]=[CH:55][N:56]=1)N=3>>[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[N:48]([CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH:47]=[C:46]([C:52]2[N:53]([CH:57]([CH3:59])[CH3:58])[N:54]=[CH:55][N:56]=2)[N:17]=4)[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 582043138-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azuleneHCID 582045883-{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

Product 1

HCID 582045373-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester

Procedure

3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-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-6-oxa-1,3a-diaza-benzo[e]azulene and 3-azetidine-1-carboxylic acid tert-butyl ester zinc iodide. LCMS: RT=4.61 min, M+H+=451.

Sources & evidence

ORD record
ord-af7dbdcb0bfc4e40a469330754d6421d
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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