N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → HCID 178438667, compound

HRID 1688672Notes

Reaction equation

[F:1][CH2:2][C:3]1([CH2:6][O:7][C@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]3[C:19](=[O:20])[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([C:28]5[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=5)=[CH:24][CH:23]=4)=[C:17]([CH2:36][CH2:37][CH3:38])[N:16]4[N:39]=[CH:40][N:41]=[C:15]34)[CH2:10][CH2:9]2)[CH2:5][O:4]1.[FH:42].[K].CCCC[N+](CCCC)(CCCC)CCCC.F.F.[F-]>ClC1C=CC=CC=1>[F:42][CH2:5][C:3]([CH2:2][F:1])([OH:4])[CH2:6][O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[C:19](=[O:20])[C:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:24][CH:23]=3)=[C:17]([CH2:36][CH2:37][CH3:38])[N:16]3[N:39]=[CH:40][N:41]=[C:15]23)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4′-{[4-(trans-4-{[2-(fluoromethyl)oxiran-2-yl]methoxy}cyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.17 g), potassium hydrogen fluoride (0.15 g), tetra-n-butylammonium dihydrogentrifluoride (0.097 g) and chlorobenzene (0.5 mL) was stirred at 120° C. for 14 hr. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.16 g, 87%).

Workup

filtrationThe precipitate was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f56801441ee941878575586304d7e8f3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148383B2

Reaction notes

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