Hydrochloric Acid → N-{2-Amino-1-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide hydrochloride

HRID 220697

Reaction equation

HRID 220697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[CH2:26][N+:27]([O-])=O)=[O:23])[N:9]=2)=[CH:4][CH:3]=1.[In].Cl>C1COCC1>[ClH:1].[NH2:27][CH2:26][CH:25]([NH:24][C:22](=[O:23])[CH2:21][N:10]1[C:11](=[O:20])[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:16])[F:17])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9]1)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:37])[F:39])[CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5359967IndiumHCID 469292312-{3-(4-Chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N-{2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

Product 1

HCID 46929233N-{2-Amino-1-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Of the compound from Example 1, 45 mg (77 μmol) and 40 mg (348 μmol) of indium powder were admixed in 0.5 ml of THF with 42 μl of conc. hydrochloric acid, and the mixture was stirred at RT for 2 h. Then the mixture was purified by preparative HPLC (Method 10). The product-containing fractions were admixed with 2 ml of 1N hydrochloric acid and concentrated on a rotary evaporator. Drying in an HV gave 21 mg (46% of theory) of the title compound as a diastereomer mixture.

Workup

  1. customThen the mixture was purified by preparative HPLC (Method 10)
  2. concentrationconcentrated on a rotary evaporator
  3. customDrying in an HV

Sources & evidence

ORD record
ord-e10e5b8ef3a34101b47dd1f7821731f3
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Linked notes

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