Tetrabutylammonium Fluoride → HCID 178428626, compound

HRID 1748652Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]2[N:38]=[CH:37][C:36]([NH:39][C:40]([C:42]3[CH:43]=[N:44][N:45]([C:48]4[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][N:49]=4)[C:46]=3[CH3:47])=[O:41])=[CH:35][C:34]=2[CH3:58])[CH2:29][CH2:28]1)(C(C)(C)C)(C)C>O1CCCC1>[OH:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]2[N:38]=[CH:37][C:36]([NH:39][C:40]([C:42]3[CH:43]=[N:44][N:45]([C:48]4[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][N:49]=4)[C:46]=3[CH3:47])=[O:41])=[CH:35][C:34]=2[CH3:58])[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 85 °C

Procedure

1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.2 ml) was added to trans-N-[6-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (41 mg) and stirred at 85° C. for six hours. After the reaction, the solvent was evaporated and the resulting residue was purified with a silica gel column chromatography (chloroform/methanol). Ethanol was added to the purified product, the precipitated solid was washed with water and dried at 60° C. in vacuo to give the titled compound (29 mg) as a white solid.

Workup

customAfter the reaction
customthe solvent was evaporated
customthe resulting residue was purified with a silica gel column chromatography (chloroform/methanol)
additionEthanol was added to the purified product
washthe precipitated solid was washed with water
customdried at 60° C. in vacuo

Sources & evidence

ORD record: ord-6fbd04d3f67e4d44b06317d3ecd15888
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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