Trifluoroacetic acid → HCID 178506160, compound

HRID 902609Notes

Reaction equation

HRID 902609 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[NH:21][N:20]=[N:19][N:18]=2)[CH:11]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[C:43]([C:44]([F:47])([F:45])[F:46])=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][N:5]([CH2:26][CH:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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[NH:21][N:20]=[N:19][N:18]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178467703HCID 178467703, compound

Product 1

HCID 178506160HCID 178506160, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[3-(ethoxymethyl-1,2,3,4-tetrazol-5-ylmethyl)-phenoxy]-propyl}-amine (mixture of regioisomers, 125 mg, 0.19 mmol) in dichloromethane (11 ml) was added triethylsilane (116 mg, 1.08 mmol). The reaction mixture was treated with TFA (3 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, acetonitrile:water, UV detection at 254 nm) to afford 50 mg (44%) the title compound as a yellow oil. MS (ESI) 607.0(M+H+).

Workup

  1. customSolvent was removed
  2. customthe residue was purified by preparative HPLC (YMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:water, UV detection at 254 nm)

Sources & evidence

ORD record
ord-5c952b57395e40a09054127033d4f803
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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