Ethanolamine → (S)-N-{3-Cyclohexyl-1-[2-(4-methoxy-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide

HRID 132133Notes

Reaction equation

HRID 132133 reaction equation
[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.[CH3:29][O:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1[CH2:33][CH2:34][NH: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:35]2[C:36]3[C:32](=[C:31]([O:30][CH3:29])[CH:39]=[CH:38][CH:37]=3)[CH2:33][CH2:34]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 74374m-Anisoyl chlorideHCID 162444414-methoxy-2,3-dihydro-1H-indoleHCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

Product 1

HCID 11409294(S)-N-{3-Cyclohexyl-1-[2-(4-methoxy-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamideYield 30%

Procedure

Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 4-methoxyindoline as starting materials, the title compound was prepared in 30% 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 0.67-0.80 (m, 2H), 0.92-1.21 (m, 6H), 1.46-1.67 (m, 6H), 1.79-1.92 (m, 1H), 2.88 (dd, 1H, J1=J2=8.1), 3.16-3.21 (m, 2H), 3.41 (dd, 1H, J1=J2=8.1), 3.51-3.43 (m, 2H), 3.71 (s, 3H), 3.73 (s, 3H), 4.44 (dd, 1H, J1=7.1, J2=13.9), 6.27 (d, 1H, J=7.9), 6.33 (d, 1H, J=8.2), 6.84-6.78 (m, 1H), 6.91-6.97 (m, 1H), 6.99 (dd, 1H, J1=J2=8.0), 7.14-7.17 (m, 2H), 7.17-7.27 (m, 3H); HPLC-MS calcd. for C29H39N3O4 (M+H+) 494.3, found 494.5.

Workup

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

Sources & evidence

ORD record
ord-dedb3b5547cc4247aff3d22787605750
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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