Tetrabutylammonium Fluoride → HCID 178467991, compound

HRID 1852827Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2-((tert-butyldimethylsilyl)oxy)-1-ethoxyethyl)-4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile was dissolved in THF (3.9 mL) and cooled to 0° C. before adding TBAF (1 M in THF, 1.5 mL). After stirring at 0° C. for 25 minutes, the reaction mixture was diluted with ethyl acetate and washed with water followed by brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (DCM/0-10% MeOH) to afford 4-(5-chloropyridin-3-yl)-2-(1-ethoxy-2-hydroxyethyl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C24H28ClN5O2 [M+H]+ 454. found 454.

Workup

washwashed with water
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (DCM/0-10% MeOH)

Sources & evidence

ORD record: ord-f9bd6381466546608ec0bfe047a54d13
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962611B2

Reaction notes

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