2-Aminoindane → 1-(5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenyl)-3-(2,3-dihydro-1H-indene-2-yl)urea

HRID 243809Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][CH:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26]1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12]([NH:24][CH:25]2[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:19])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2,2,2-trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate (0.096 g, 0.250 mmol) and 2-aminoindane (0.033 g, 0.248 mmol) in acetonitrile (1.0 mL), N,N-diisopropylethylamine (0.065 mL, 0.38 mmol) was added, and the mixture was stirred at 70° C. for 12 hours. The reaction mixture was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-60/40) to obtain 0.092 g (quantitative) of the captioned compound.

Workup

customThe reaction mixture was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-60/40)
customto obtain 0.092 g (quantitative) of the captioned compound

Sources & evidence

ORD record: ord-1591d1f354ad4c3c8f74ce94fd7a69ac
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653304B2

Reaction notes

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