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

HRID 132129Notes

Reaction equation

HRID 132129 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:32]=[CH:33][CH:34]=[C:35]2[C:39]=1[NH:38][CH2:37][CH2:36]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:38]2[C:39]3[C:35](=[CH:34][CH:33]=[CH:32][C:31]=3[O:30][CH3:29])[CH2:36][CH2:37]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 74374m-Anisoyl chlorideHCID 148495547-Methoxy-2,3-dihydro-1H-indoleHCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

Product 1

HCID 11477436(S)-N-{3-Cyclohexyl-1-[2-(7-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 7-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 0.78-0.92 (m, 2H), 1.05-1.32 (m, 6H), 1.59-1.81 (m, 6H), 1.94-2.05 (m, 1H), 3.10-3.20 (m, 2H), 3.45-3.72 (m, 5H), 3.80 (s, 3H), 3.86 (s, 3H), 4.62 (dd, 1H, J1=7.8, J2=13.7), 6.78 (d, 1H, J1=8.2), 6.86 (d, 1H, J1=7.2), 7.00-7.08 (m, 2H), 7.18-7.23 (m, 1H), 7.30-7.47 (m, 3H), 7.53-7.62 (m, 1H); 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-538aff4e482b4b8e8f51d446e78a7104
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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