Trifluoroacetic acid → Ammonium Hydroxide

HRID 1421709Notes

Reaction equation

HRID 1421709 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:39])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]=[CH:17][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=3)=[CH:10][N:9]=2)[CH:7]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[NH4+:6].[OH-:39].[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:39])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]=[CH:17][NH:18][CH:19]=3)=[CH:10][N:9]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 178516065HCID 178516065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23 step 5 (1.00 g, 1.89 mmol) in CH2Cl2 (15 mL) was added trifluoroacetic acid (0.86 g, 7.6 mmol) and the dark yellow solution was stirred for 5 min at ambient temperature. Triethylsilane was added dropwise until the yellow color was dissipated and the solution was concentrated in vacuo. The residue was purified by flash column chromatography, eluting with CH2Cl2 ; 1% MeOH; 0.1% NH4OH, to give the title compound:

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was purified by flash column chromatography
  3. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-a48a285c5a534cc98fb014d9d87920eb
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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