Chlorobenzene → HCID 178438666, compound

HRID 2048442Notes

Reaction equation

HRID 2048442 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:17](=[O:18])[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:22][CH:21]=3)=[C:15]([CH2:34][CH2:35][CH3:36])[N:14]3[N:37]=[CH:38][N:39]=[C:13]23)[CH2:8][CH2:7]1.[FH:40].[K].CCCC[N+](CCCC)(CCCC)CCCC.F.F.[F-].ClC1C=CC=CC=1>C1(C)C=CC=CC=1>[F:40][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:17](=[O:18])[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:22][CH:21]=3)=[C:15]([CH2:34][CH2:35][CH3:36])[N:14]3[N:37]=[CH:38][N:39]=[C:13]23)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)2×HCID 53443437Potassium fluoride, 99%, spray-dried2×HCID 178438598HCID 178438598, compound

Product 1

HCID 178438666HCID 178438666, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4′-({4-[trans-4-(oxiran-2-ylmethoxy)cyclohexyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.25 g), potassium hydrogen fluoride (0.075 g), tetra-n-butylammonium dihydrogentrifluoride (0.015 g) and chlorobenzene (1 mL) was stirred at 120° C. for 5 hr. Potassium hydrogen fluoride (0.075 g) and tetra-n-butylammonium dihydrogentrifluoride (0.014 g) were added, and the mixture was stirred at 120° C. for 16 hr. Toluene was added, and the precipitate was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.15 g, 60%).

Workup

  1. stirringthe mixture was stirred at 120° C. for 16 hr
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-065b5e51422349509a95e90b07fdccb9
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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