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

HRID 1688672
Notes
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Reaction equation

HRID 1688672 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 53443437Potassium fluoride, 99%, spray-driedHCID 178438596HCID 178438596, compound

Product 1

HCID 178438667HCID 178438667, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 7964
Chlorobenzene
Solvent

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

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes