1,1'-Carbonyldiimidazole → 8-{3-[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]phenyl}-6-[1-methyl-1-(methylsulfonyl)ethyl]quinoline

HRID 1455661Notes

Reaction equation

[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=O)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].C1N=CN(C(N2C=NC=C2)=O)C=1.[F:39][C:40]1[CH:45]=[CH:44][C:43]([C:46](=[N:48]O)[NH2:47])=[CH:42][CH:41]=1>CN(C=O)C.O>[F:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[N:48]=[C:21]([C:20]3[CH:19]=[C:18]([C:16]4[CH:17]=[C:8]([C:2]([CH3:1])([S:4]([CH3:7])(=[O:5])=[O:6])[CH3:3])[CH:9]=[C:10]5[C:15]=4[N:14]=[CH:13][CH:12]=[CH:11]5)[CH:26]=[CH:25][CH:24]=3)[O:23][N:47]=2)=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of acid from step 2 in DMF (0.05M) was added CDI (2 eq) and 4-fluoro-N′-hydroxybenzenecarboximidamide (2 eq). The reaction mixture was stirred at rt for 15 min and 18 h at 120° C. The reaction mixture cooled to rt, diluted with water and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (hexane:EtOAc, 20:80) to afforded the title compound.

Workup

temperatureThe reaction mixture cooled to rt
extractionextracted with EtOAc
washThe organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (hexane:EtOAc, 20:80)

Sources & evidence

ORD record: ord-a1eecee1a3574204989fb0e0bd026a4a
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482456B2

Reaction notes

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