Diethyl Ether → HCID 10155691, compound

HRID 1166694Notes

Reaction equation

HRID 1166694 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]([CH:16]([CH3:18])[CH3:17])[C:6]=2[CH:5]=1)[CH3:2].F[C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=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]([CH:16]([CH3:17])[CH3:18])[C:6]=2[CH:5]=1)[C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2428196-Fluoronicotinic AcidHCID 22218222HCID 22218222, compound2×

Product 1

HCID 10155691HCID 10155691, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of 85 mg (0.35 mmol) of ethyl-(8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-amine (Compound 168) and 0.10 g (0.71 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. Purification was done using 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 (26 mg).

Workup

  1. temperatureThe mixture was cooled
  2. customPurification
  3. customfollowed by recrystallization

Sources & evidence

ORD record
ord-34c3ed8080ad4740a1606d2f3763d9da
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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