Ethanolamine → (S)-N-{3-Cyclohexyl-1-[2-(7-fluoro-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide

HRID 132131

Reaktionsgleichung

Reaktionsgleichung von HRID 132131
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[NH2:12][C@@H:13]([CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:14]([OH:16])=O.[CH2:25]([CH2:27][NH2:28])O.[F:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH2:36][CH2:35]2>>[CH:19]1([CH2:18][CH2:17][C@H:13]([NH:12][C:1](=[O:10])[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=2)[C:14](=[O:16])[NH:28][CH2:27][CH2:25][N:37]2[C:38]3[C:34](=[CH:33][CH:32]=[CH:31][C:30]=3[F:29])[CH2:35][CH2:36]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 4

HCID 700EthanolamineHCID 74374m-Anisoyl chlorideHCID 167682617-Fluoro-2,3-dihydro-1H-indoleHCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

Produkt 1

HCID 11306188(S)-N-{3-Cyclohexyl-1-[2-(7-fluoro-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamideAusbeute 40 %

Versuchsvorschrift

Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 7-fluoroindoline as starting materials, the title compound was prepared in 40% yield. The final material was purified by reverse phase preparative HPLC using TFA as a modifier. The final compound is therefore a partial TFA salt and the properties are reported for the material as it appeared after solvent removal: 1H NMR (CDCl3, 400 MHz) δ 0.73-0.87 (m, 2H), 1.03-1.28 (m, 6H), 1.58-1.78 (m, 6H), 1.83-1.95 (m, 1H), 3.01 (dd, 2H, J1=J2=8.4), 3.41-3.50 (m, 4H), 3.55-3.72 (m, 1H), 3.84 (s, 3H), 4.63 (dd, 1H, J1=7.1, J2=14.3), 6.53-6.68 (m, 2H), 6.78 (dd, 1H, J1=8.5, J2=12.3), 6.86 (d, 1H, J1=7.0), 7.01-7.08 (m, 2H), 7.20 (d, 1H, J1=7.8), 7.26-7.39 (m, 3H); HPLC-MS calcd. for C28H36FN3O3 (M+H+) 482.3, found 482.5.

Aufarbeitung

  1. customThe final material was purified by reverse phase preparative HPLC
  2. customafter solvent removal

Quellen und Nachweise

ORD-Eintrag
ord-858203832a76421cbfccc818a80c7811
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384970B2

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