Trifluoroacetic acid → HCID 86653130, compound

HRID 1258574Notes

Reaction equation

HRID 1258574 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][N:25]=[C:26]([C:33]3[N:37]([CH3:38])[N:36]=[N:35][N:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:18]=2)C(=O)OC(C)(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([CH2:7][CH2:8][NH:9][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][N:25]=[C:26]([C:33]3[N:37]([CH3:38])[N:36]=[N:35][N:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86653129HCID 86653129, compound

Product 1

HCID 86653130HCID 86653130, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (2-cyclohexylethyl){6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (0.252 g, 0.413 mmol, 1 eq.) in 5 ml of dry DCM, was added TFA (1.41 g, 12.39 mmol, 30 eq.) in one portion. The reaction was refluxed for 5 hrs. Then the solvent and excess TFA were evaporated. The residue was neutralised with TEA and purified by chromatography on silica gel to give N-(2-cyclohexylethyl)-6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (0.138 g, 76% yield) as a viscous oil.

Workup

  1. temperatureThe reaction was refluxed for 5 hrs
  2. customThen the solvent and excess TFA were evaporated
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-54d9ebce8dc44bfc88bf613fdb228cf2
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

Loading…