Trifluoroacetic acid → 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-(piperidin-4-ylsulfanyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530365Notes

Reaction equation

HRID 1530365 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[CH:17][C:18]3[O:27][CH2:26][CH2:25][N:24]4[C:20](=[N:21][C:22]([C:28]5[N:29]([CH:33]([CH3:35])[CH3:34])[N:30]=[CH:31][N:32]=5)=[CH:23]4)[C:19]=3[CH:36]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:33]([N:29]1[C:28]([C:22]2[N:21]=[C:20]3[N:24]([CH2:25][CH2:26][O:27][C:18]4[CH:17]=[CH:16][C:15]([S:14][CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[CH:36][C:19]=43)[CH:23]=2)=[N:32][CH:31]=[N:30]1)([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 683130254-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl]piperidine-1-carboxylic acid tertbutyl ester

Product 1

HCID 683129382-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-(piperidin-4-ylsulfanyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azuleneYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cooled solution of 4-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl]piperidine-1-carboxylic acid tertbutyl ester (0.722 g) in DCM (10 mL) was treated with TFA (2 mL) and stirred at RT for 2 h. Volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (C18, gradient 20-50% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH affording 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-(piperidin-4-ylsulfanyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (0.368 g). LCMS: RT 2.08/2.14 min [M+H]+ 411.2

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was purified by column chromatography (C18, gradient 20-50% MeOH in 0.5% TFA/H2O)
  3. washThe cartridge was washed with MeOH
  4. washthe product eluted with 0.5M NH3/MeOH

Sources & evidence

ORD record
ord-71b0afbd17b54a29be93fa24fa3a4b0d
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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