Water → 8-Azetidin-3-yl-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1190730Notes

Reaction equation

HRID 1190730 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]2[CH:34]=[CH:33][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:30]([CH3:32])[CH3:31])[N:26]=[C:27]([CH3:29])[N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.O.C(OCC)(=O)C>C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([C:12]2[CH:34]=[CH:33][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:30]([CH3:32])[CH3:31])[N:26]=[C:27]([CH3:29])[N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 582040483-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 582041048-Azetidin-3-yl-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester (4.11 g, 0.01234 mol) in methylene chloride (42 mL) was added trifluoroacetic acid (20 mL) dropwise. The reaction was stirred at room temperature for 1 hour. Water and ethyl acetate were added and the mixture was extracted with 1N HCl. The aqueous phase was basified to pH 13 with 1N NaOH. The aqueous phase was filtered and rinsed with cold water to afford 8-azetidin-3-yl-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene as an off-white solid (3.2 g). MS (ESI+) 382.2

Workup

  1. extractionthe mixture was extracted with 1N HCl
  2. filtrationThe aqueous phase was filtered
  3. washrinsed with cold water

Sources & evidence

ORD record
ord-fbf951440fb84e3e997ad06845a59426
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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