Trifluoroacetic acid → HCID 178522994, compound

HRID 1360197Notes

Reaction equation

HRID 1360197 reaction equation
COC1C=C(C=CC=1OC)C[N:7]1[C:11]2=[N:12][CH:13]=[C:14]([C:28]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[O:29])[C:15]([NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][C:22]([OH:27])([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)=[C:10]2[N:9]=[CH:8]1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>>[F:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][NH:30][C:28]([C:14]2[C:15]([NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][C:22]([OH:27])([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)=[C:10]3[N:9]=[CH:8][NH:7][C:11]3=[N:12][CH:13]=2)=[O:29])=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66924312HCID 66924312, compound

Product 1

HCID 178522994HCID 178522994, compoundYield 24.5%

Procedure

To 3-(3,4-dimethoxybenzyl)-N-(4-fluorobenzyl)-7-{(5-hydroxyadamantan-2-yl)amino}-3H-imidazo[4,5-b]pyridine-6-carboxamide (170 mg) was added trifluoroacetic acid (1.7 ml), and the mixture was stirred at ambient temperature for overnight. The reaction solution was neutralized with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate and tetrahydrofuran. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol) to obtain N-(4-fluorobenzyl)-7-{(5-hydroxyadamantan-2-yl)amino}-3H-imidazo[4,5-b]pyridine-6-carboxamide (31 mg).

Workup

  1. extractionextracted with ethyl acetate and tetrahydrofuran
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-2e064a374b7d4a97a020f6171bb96ac1
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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