Trifluoroacetic acid → HCID 10044232, compound

HRID 2055086Notes

Reaction equation

HRID 2055086 reaction equation
[CH:1]1([NH:4][C:5]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[CH:20][CH:19]=2)[CH2:3][CH2:2]1.[OH-].[K+].FC(F)(F)C(O)=O>CO>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([N:9]2[CH:8]=[N:7][C:6]3[C:10]2=[N:11][C:12]([C:14]([F:17])([F:15])[F:16])=[N:13][C:5]=3[NH:4][CH:1]2[CH2:3][CH2:2]2)=[CH:23][CH:22]=1)([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 10339538HCID 10339538, compound

Product 1

HCID 10044232HCID 10044232, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Cyclopropylamino-9-(4-methoxycarbonylphenyl)-2-trifluoromethylpurine (20 mg, 0.053 mmol) was treated with 0.53 mmol of 1-2 M KOH in methanol (containing 5% water) and stirred for 14 hours at room temperature. The reaction mixture was acidified with trifluoroacetic acid (30% in dichloromethane) to pH=2 and concentrated under vacuum. The residue was extracted with 20% methanol in dichloromethane. The extraction was loaded on a silica gel column and eluted with 20% methanol in dichloromethane to give 9-(4-carboxyphenyl)-6-cyclopropylamino-2-trifluoromethylpurine (14 mg, 70% yield). 1H NMR (300 MHz, DMSO) δ 8.85 (s, 1H), 8.70 (s, 1H), 8.15 (d, J=8.4 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 3.07 (b, 1H), 0.78 (b, 2H), 0.68 (b, 2H). [ESMS m/z (363.9 (M+1)+)]

Workup

  1. concentrationconcentrated under vacuum
  2. extractionThe residue was extracted with 20% methanol in dichloromethane
  3. extractionThe extraction
  4. washeluted with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-ef1b8cfafa484870830c4afb6f800684
Source dataset
uspto-grants-2008_02
Patent number
US07332486B2

Reaction notes

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