Tetrabutylammonium Fluoride → 5-[6-(hydroxymethyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[1-(2-methylphenyl)ethoxy]thiophene-2-carboxamide

HRID 2391636Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([O:27][CH:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])[CH3:29])[CH:20]=3)[C:12]=2[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([O:27][CH:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])[CH3:29])[CH:20]=3)[C:12]=2[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 650 mg of 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[1-(2-methylphenyl)ethoxy]thiophene-2-carboxamide in 50 ml THF is cooled to 0° C. At 0° C. 0.45 ml tetra-n-butylammonium fluoride (˜75% in H20) is added. The reaction mixture is allowed to warm to room temperature and stirred over night.

Workup

customAt 0° C
temperatureto warm to room temperature

Sources & evidence

ORD record: ord-0657e9bd04fe436c90aa5ca291984c19
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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