Diethyl Ether → HCID 9924555, compound

HRID 1166693Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH:8]=[C:7]([CH2:16][CH3:17])[C:6]=2[CH:5]=1)[CH3:2].F[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][N:20]=1.CCOCC>C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH:8]=[C:7]([CH2:16][CH3:17])[C:6]=2[CH:5]=1)[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][N:20]=1)[CH3:2]

Participants

Conditions

Temperature: 125 °C

Procedure

To a mixture of 0.35 g (1.5 mmol) ethyl-(8-ethyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-amine (Compound 167 and 0.32 g (2.2 mmol) of 6-fluoro-nicotinic acid was added a small amount of ether and toluene to help stirring. The resulting mixture was heated at 100-150° C. for 1 h. The mixture was cooled. The product was purified by flash chromatography (silica, 50% ethyl acetate in hexanes) followed by recrystallization using ethyl acetate:hexane (1:1) to give the title compound as white crystals (22 mg).

Workup

temperatureThe mixture was cooled
customThe product was purified by flash chromatography (silica, 50% ethyl acetate in hexanes)
customfollowed by recrystallization

Sources & evidence

ORD record: ord-07beae2976f14d968c4d7c98b756da47
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613917B1

Reaction notes

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