Trifluoroacetic acid → 1-isopropyl-1H-imidazo[4,5-c]pyridin-6-amine
Reaction equation
FC(F)(F)C(O)=O.[CH:8]([N:11]1[C:19]2[CH:18]=[C:17]([NH:20]CC3C=CC(OC)=CC=3)[N:16]=[CH:15][C:14]=2[N:13]=[CH:12]1)([CH3:10])[CH3:9]>C(Cl)Cl>[CH:8]([N:11]1[C:19]2[CH:18]=[C:17]([NH2:20])[N:16]=[CH:15][C:14]=2[N:13]=[CH:12]1)([CH3:10])[CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Trifluoroacetic acid (2.42 ml, 31.4 mmol) was added to a solution of 1-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine (intermediate 25, 596 mg, 2.01 mmol) in DCM (12 ml) and then the mixture was stirred at 40° C. for 24 h. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3 (strong gas evolution) and H2O. The aqueous phase was extracted with DCM (2×). The combined organic layers were dried over Na2SO4 and evaporated. The crude material was applied to a 24 g RediSep® silica column and purified by normal phase chromatography, eluting with 9:1 CH2Cl2/MeOH. Product-containing fractions were combined and evaporated to give the title compound as a beige solid. (UPLC-MS 6) tR 0.33; ESI-MS 177.1 [M+H]+.
Workup
- washwashed with sat. aq. NaHCO3 (strong gas evolution) and H2O
- extractionThe aqueous phase was extracted with DCM (2×)
- dry with materialThe combined organic layers were dried over Na2SO4
- customevaporated
- custompurified by normal phase chromatography
- washeluting with 9:1 CH2Cl2/MeOH
- customevaporated
Sources & evidence
- ORD record
- ord-3665b3dd60ef4c95a35e214625261c39
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266883B2
Reaction notes
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