Ethanolamine → (S)-N-{3-Cyclohexyl-1-[2-(6-fluoro-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide

HRID 132130

反応式

HRID 132130 の反応式
[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:38]=[C:37]2[C:33]([CH2:34][CH2:35][NH:36]2)=[CH:32][CH:31]=1>>[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:36]2[C:37]3[C:33](=[CH:32][CH:31]=[C:30]([F:29])[CH:38]=3)[CH2:34][CH2:35]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

参加物

5

反応物 4

HCID 700EthanolamineHCID 74374m-Anisoyl chlorideHCID 2604006-fluoro-2,3-dihydro-1H-indoleHCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

生成物 1

HCID 11375074(S)-N-{3-Cyclohexyl-1-[2-(6-fluoro-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide収率 40%

実験手順

Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 6-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 0.72-0.86 (m, 2H), 1.03-1.28 (m, 6H), 1.58-1.69 (m, 6H), 1.85-1.96 (m, 1H), 2.89 (dd, 2H, J1=J2=8.1), 3.19 (dd, 2H, J1=J2=6.0), 3.43 (dd, 2H, J1=J2=8.4), 3.37-3.47 (m, 1H), 3.53-3.62 (m, 1H), 3.84 (s, 3H), 4.64 (dd, 1H, J1=7.0, J2=14.1), 6.16 (d, 1H, J=10.2), 6.26-6.33 (m, 1H), 6.92 (dd, 1H, J1=J2=6.7), 7.02-7.07 (m, 2H), 7.12-7.19 (m, 2H), 7.26-7.39 (m, 3H); HPLC-MS calcd. for C28H36FN3O3 (M+H+) 482.3, found 482.5.

後処理

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

出典と根拠

ORDレコード
ord-8f9a2a7cb0e3420c91545a0f33d5075a
出典データセット
uspto-grants-2008_06
特許番号
US07384970B2

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