Trifluoroacetic acid → HCID 68312736, compound

HRID 1530502Notes

Reaction equation

HRID 1530502 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:20][CH2:19][CH2:18][N:17]3[C:13](=[N:14][C:15]([C:21]4[N:22]([CH:26]([CH3:28])[CH3:27])[N:23]=[CH:24][N:25]=4)=[CH:16]3)[C:12]=2[CH:29]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:26]([N:22]1[C:21]([C:15]2[N:14]=[C:13]3[N:17]([CH2:18][CH2:19][O:20][C:11]4[CH:10]=[CH:9][C:8]([CH2:7][C:6]([OH:30])=[O:5])=[CH:29][C:12]=43)[CH:16]=2)=[N:25][CH:24]=[N:23]1)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68312683HCID 68312683, compound

Product 1

HCID 68312736HCID 68312736, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]acetic acid tert-butyl ester (930 mg, 2.27 mmol) in DCM (20 mL) was added TFA (10 mL) and the resulting mixture stirred at RT for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was found to be acid and the corresponding methyl ester so was purified by column chromatography (Si-PCC, gradient 0-20% MeOH in DCM) affording [2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]acetic acid as a white solid (164 mg, 21%). LCMS: RT 2.65 min [M+H]+ 354.3

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH
  3. customthe corresponding methyl ester so was purified by column chromatography (Si-PCC, gradient 0-20% MeOH in DCM)

Sources & evidence

ORD record
ord-e3446699b9d64d2281e00f411b89da38
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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