Isobutylamine → HCID 58731015, Verbindung

HRID 269563

Reaktionsgleichung

Reaktionsgleichung von HRID 269563
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[C:20]2[C:21]([C:26]3[CH:31]=[C:30]([C:32]([O:34]C)=O)[CH:29]=[C:28]([C:36]([OH:38])=[O:37])[CH:27]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1.[CH3:39]N1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCC(N=C=N)C.[CH2:69]([NH2:73])[CH:70]([CH3:72])[CH3:71]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][C:11]=2[C:20]2[C:21]([C:26]3[CH:31]=[C:30]([C:32]([NH:73][CH2:69][CH:70]([CH3:72])[CH3:71])=[O:34])[CH:29]=[C:28]([C:36]([O:38][CH3:39])=[O:37])[CH:27]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 6558IsobutylamineHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 587310142''-{[(4-Fluorophenyl)methyl]oxy}-5-[(methyloxy)carbonyl]-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-3-carboxylic acid

Produkt 1

HCID 58731015HCID 58731015, VerbindungAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2″-{[(4-fluorophenyl)methyl]oxy}-5-[(methyloxy)carbonyl]-5″-(trifluoromethyl)-1,1′:2′,1″-terphenyl-3-carboxylic acid (90 mg, 0.17 mmol), 4-methylmorpholine (34 mg, 45 μl, 0.34 mmol), 1-hydroxybenzotriazole hydrate (30 mg, 0.2 mmol), 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (38 mg, 0.2 mmol), and isobutylamine (25 mg, 34 ul, 0.34 mmol) in dichloromethane (3 ml) was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (10 ml), then washed with saturated NaHCO3, 2M HCl, water and brine. The organic phase was dried and evaporated. The residue was purified by chromatography in ethyl acetate/hexane (1:9-1:4) to give the title compound as a colourless solid (51 mg, 50%). LCMS: Rt=4.10 min. [M+H] 580

Aufarbeitung

  1. washwashed with saturated NaHCO3, 2M HCl, water and brine
  2. customThe organic phase was dried
  3. customevaporated
  4. customThe residue was purified by chromatography in ethyl acetate/hexane (1:9-1:4)

Quellen und Nachweise

ORD-Eintrag
ord-4047a240d5c644808cfa34e5e1c68e3f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446222B2

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