Trifluoroacetic acid → Trifluoroacetic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH3:15])[C:12]([CH3:16])=[C:11]([NH:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[CH2:24][NH:25][N:26](CC4C=CC(OC)=CC=4)[C:19]=23)[CH:10]=1.FC1C=CC(F)=CC=1C1N=C(C)C(C)=C(NC2C3C(=CN(CC4C=CC(OC)=CC=4)N=3)N=CC=2)C=1.[C:71]([OH:77])([C:73]([F:76])([F:75])[F:74])=[O:72]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH3:15])[C:12]([CH3:16])=[C:11]([NH:17][C:18]2[C:19]3[C:20](=[CH:24][NH:25][N:26]=3)[N:21]=[CH:22][CH:23]=2)[CH:10]=1.[C:71]([OH:77])([C:73]([F:76])([F:75])[F:74])=[O:72]Participants
Reactant 3
Product 2
Conditions
- Temperature
- 70 °C
Procedure
N-(6-(2,5-Difluorophenyl)-2,3-dimethylpyridin-4-yl)-1-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and N-(6-(2,5-difluorophenyl)-2,3-dimethylpyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine was combined in TFA (5 mL) and heated at 70° C. for 12 hours. The reaction mixture was evaporated to give a residue which was purified via preparative HPLC using a gradient of 5-30% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column to give the title compound as a TFA salt. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.93 (s, 1H) 2.24 (s, 1H) 2.42 (s, 3H) 2.75 (s, 3H) 6.96 (br. s., 1H) 7.23-7.33 (m, 2H) 7.60 (s, 1H) 7.61-7.68 (m, 1H) 8.44 (s, 2H). MS [M+H] found 352.1
Workup
- customThe reaction mixture was evaporated
- customto give a residue which
- customwas purified via preparative HPLC
Sources & evidence
- ORD record
- ord-1e3c107054c14b348eac4b14fa7e9915
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073918B2
Reaction notes
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