Trifluoroacetic acid → ethyl(3-(4-hydroxy-3-methoxybenzyl)-6-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

HRID 706486Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:40])[NH:5][C:6]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28]CC3C=CC(OC)=CC=3)=[C:24]([O:38][CH3:39])[CH:23]=2)[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)[CH:13]=[C:8]2[N:7]=1)[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:1]([O:3][C:4](=[O:40])[NH:5][C:6]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([O:38][CH3:39])[CH:23]=2)[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)[CH:13]=[C:8]2[N:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl(3-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-6-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (2.50 g, 4.61 mmol) in dichloromethane (100 mL) at 0° C. was added trifluoroacetic acid (4.47 g, 3.0 mL, 39.18 mmol). The resulting mixture was allowed to stir at 0° C. After 2 h, the mixture was treated with 2M potassium carbonate solution to adjust the pH to ˜9. The basic mixture was extracted with 1:1 methanol/dichloromethane solution (2×50 mL). The combined organic phases were washed with brine (2×50 mL), dried over sodium sulfate, filtered, and concentrated to provide 1.80 g (93%) of ethyl(3-(4-hydroxy-3-methoxybenzyl)-6-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate as a white solid.

Workup

extractionThe basic mixture was extracted with 1:1 methanol/dichloromethane solution (2×50 mL)
washThe combined organic phases were washed with brine (2×50 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-44705443676d4b7485bc03509345efed
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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