Trifluoroacetic acid → HCID 178506205, compound

HRID 2252005Notes

Reaction equation

HRID 2252005 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[N:19]=[N:20][NH:21][C:22]=2[CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])O)[N:9]=[N:8]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:36])([F:38])[F:37])[CH:34]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[N:19]=[N:20][NH:21][C:22]=2[CH2:23][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[N:9]=[N:8]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 178519522HCID 178519522, compound

Product 1

HCID 178506205HCID 178506205, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve [1′-(3,5-bis-trifluoromethyl-benzyl)-5′-phenyl-1H,1′H-[4,4′]bi[[1,2,3]triazolyl]-5-yl]-(2-chloro-phenyl)-methanol (38 mg, 0.066 mmol) and 1.5 mL CH2Cl2. Carefully add triethylsilane (23 mg, 31.4 μL, 0.197 mmol). Cool to 0° C. and add trifluoroacetic acid (452 mg, 305 μL, 3.96 mmol) and stir. After 15 hours, pour into 10 mL of (saturated aqueous NaHCO3) and 20 mL of CH2Cl2. Extract 3 times with CH2Cl2 and 1 time with EtOAc. Combine the organics, dry over MgSO4 and filter and concentrate. Apply the mixture to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a 100 mL of Hexanes, and then 200 mL each of of 10:90 EtOAc/Hexanes, 20:80 EtOAc/Hexanes, 30:70 EtOAc/Hexanes, 50:50 Hexanes/EtOAc to provide the title compound. Exact Mass 562.1: mass spectrum (IS): m/z=563.1 (M+1), 561.1 (M−1); 1H NMR (250 MHz, CDCl3) 7.72 (s, 1H), 7.42-7.28 (m, 5H), 7.24 (m, 1H), 7.16-6.97 (m, 6H), 5.52 (s, 2H), 4.37 (s, 2H).

Workup

  1. extractionExtract 3 times with CH2Cl2 and 1 time with EtOAc
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. washApply the mixture to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a 100 mL of Hexanes

Sources & evidence

ORD record
ord-63791b5c7f23480ebdfbb6edb2e4392f
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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