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Hydrochloric Acid → 8-Azetidin-3-yl-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene hydrochloride

HRID 886077
Notes
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Reaction equation

HRID 886077 reaction equation
C(OC([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]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])[N:26]=[CH:27][N:28]=2)[N:17]=4)[CH2:9]1)=O)(C)(C)C.[ClH:39]>O1CCOCC1>[ClH:39].[NH: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]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])[N:26]=[CH:27][N:28]=2)[N:17]=4)[CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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 670506218-Azetidin-3-yl-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

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 (1.1 g, 2.11 mmol) was dissolved in hydrochloric acid in dioxane (10 mL, 4N) and the reaction stirred at RT for 1 h. After approximately 5 min a thick white precipitate formed. The reaction was concentrated in vacuo to yield 8-Azetidin-3-yl-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene hydrochloride as a yellow solid (1.0 g, 100%). LCMS: RT=3.00 min, M+H+=421.

Workup

  1. customAfter approximately 5 min a thick white precipitate formed
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-5edcdf1f28624bbcbc5cb0df85639191
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242104B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes