Trifluoroacetic acid → HCID 54571029, compound

HRID 1858178Notes

Reaction equation

HRID 1858178 reaction equation
C([O:5]C([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([C:27](=[O:35])[NH:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][N:30]=3)[CH:25]=2)[NH:20][C:19](=[O:37])[C:18]=1[C:38]1[S:39][C:40]([Cl:43])=[CH:41][CH:42]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[OH-:5].[NH4+:8].[N:32]1[CH:33]=[CH:34][C:29]([NH:28][C:27]([C:24]2[CH:25]=[C:26]3[C:21](=[CH:22][C:23]=2[Cl:36])[NH:20][C:19](=[O:37])[C:18]([C:38]2[S:39][C:40]([Cl:43])=[CH:41][CH:42]=2)=[C:17]3[O:16][CH2:15][CH2:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]2)=[O:35])=[N:30][CH:31]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54269752HCID 54269752, compound

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 54571029HCID 54571029, compoundYield 133.7%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of 2-{2-[7-chloro-3-(5-chlorothiophen-2-yl)-2-oxo-6-(pyrimidin-4-ylcarbamoyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (17 mg in 1.0 dry methylene chloride) was added a few drops of anisole followed by 0.5 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 0.5 hours, the solvents were removed in vacuo and the resulting residue purified flash chromatography on silica gel (methylene chloride:methanol, 97:3+1% ammonium hydroxide; then 95:5+1% ammonium hydroxide; then 90:10+1% ammonium hydroxide) to give the title compound (9.6 mg). MASS: 545 (M+H)

Workup

  1. customthe solvents were removed in vacuo
  2. customthe resulting residue purified flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-6705519586004d0f9c7b1f425fcdbb02
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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