Trifluoroacetic acid → HCID 178478966, compound

HRID 902607Notes

Reaction equation

HRID 902607 reaction equation
[Cl:1][C:2]1[C:43]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][N:5]([CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16](COCC)[C:17]2[N:21]=[CH:20][NH:19][N:18]=2)[CH:11]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.Cl.C(OCC)C>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[C:43]([C:44]([F:45])([F:46])[F:47])=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][N:5]([CH2:26][CH:27]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]2[N:21]=[CH:20][NH:19][N:18]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 10953452Ether hydrochlorideHCID 178467702HCID 178467702, compound

Product 1

HCID 178478966HCID 178478966, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[3-(ethoxymethyl-1,2,4-triazol-3-ylmethyl)-phenoxy]-propyl)amine (mixture of regioisomers, 90 mg, 0.135 mmol) in dichloromethane (1.5 mL) was added triethylsilane (157 mg, 1.35 mmol). The reaction mixture was treated with TFA (0.5 mL) and then stirred overnight Solvent was removed and the residue was purified by preparative HPLC (YMC CombiPrep PDS, 75×30 mm, 25 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, UV detection at 254 nm) to give an oil. The oil was dissolved in diethyl ether and acidified with 1.0 M HCl/diethyl ether to give 40 mg (48% yield) of the title compound as a yellow oil. MS (ESI) 605.0 (M+).

Workup

  1. customwas removed
  2. customthe residue was purified by preparative HPLC (YMC CombiPrep PDS, 75×30 mm, 25 mL/min
  3. waitA: acetonitrile B: water, A: 60 to 100% during 10 min
  4. customUV detection at 254 nm) to give an oil

Sources & evidence

ORD record
ord-8d11844b2ce84538a358ed73d3f00c90
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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