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

HRID 1530515Notes

Reaction equation

HRID 1530515 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]3[O:29][CH2:28][CH2:27][N:26]4[C:22](=[N:23][C:24]([C:30]5[N:31]([CH:35]([CH3:37])[CH3:36])[N:32]=[CH:33][N:34]=5)=[CH:25]4)[C:21]=3[CH:38]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:35]([N:31]1[C:30]([C:24]2[N:23]=[C:22]3[N:26]([CH2:27][CH2:28][O:29][C:20]4[CH:19]=[CH:18][C:17]([S:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)(=[O:15])=[O:16])=[CH:38][C:21]=43)[CH:25]=2)=[N:34][CH:33]=[N:32]1)([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68312738HCID 68312738, compound

Product 1

HCID 683126992-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-(piperazine-1-sulfonyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azuleneYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonyl]piperazine-1-carboxylic acid tert-butyl ester (175 mg, 0.32 mmol) in DCM (3 mL) was treated with TFA (3 mL) and the resulting mixture stirred at RT for 1 h then concentrated in vacuo. The resulting residues was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and eluted with 2M NH3/MeOH affording 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-9-(piperazine-1-sulfonyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (126 mg, 88%). LCMS: RT 2.20 and 0.32 min [M+H]+ 444.3

Workup

  1. concentrationthen concentrated in vacuo
  2. washwas washed with MeOH
  3. washeluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-ca5344172a43448aa3e731b03d780502
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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