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

HRID 2391635Notes

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][CH2:28][C:29]4[CH:34]=[C:33]([O:35][CH2:36][CH3:37])[CH:32]=[CH:31][C:30]=4[O:38][CH2:39][CH3:40])[CH:20]=3)[C:12]=2[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:39]([O:38][C:30]1[CH:31]=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[CH:34][C:29]=1[CH2:28][O:27][C:21]1[CH:20]=[C:19]([N:18]2[C:12]3[CH:11]=[C:10]([CH2:9][OH:8])[N:15]=[CH:14][C:13]=3[N:16]=[CH:17]2)[S:23][C:22]=1[C:24]([NH2:26])=[O:25])[CH3:40]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 450 mg of 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[(2,5-diethoxybenzyl)oxy]thiophene-2-carboxamide in 20 ml THF is cooled to 0° C. At 0° C. 0.28 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-4bcde9f499034051b5395162be2c43cc
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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