Ethanolamine → (2S)-4-cyclohexyl-N-[2-(5-fluoro-2,3-dihydro-1H-indol-1-yl)ethyl]-2-[(3-methoxyphenyl)formamido]butanamide

HRID 132135Notes

Reaction equation

HRID 132135 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.[F:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][CH2:34][CH2:33]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](=[CH:31][C:30]([F:29])=[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 27744635-FluoroindolineHCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

Product 1

HCID 11784942(2S)-4-cyclohexyl-N-[2-(5-fluoro-2,3-dihydro-1H-indol-1-yl)ethyl]-2-[(3-methoxyphenyl)formamido]butanamideYield 40%

Procedure

Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 5-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 0.50-0.65 (m, 2H), 0.79-1.05 (m, 6H), 1.33-1.53 (m, 6H), 1.60-1.74 (m, 1H), 2.70 (dd, 2H, J1=J2=8.1), 2.94 (dd, 2H, J1=J2=6.0), 3.15 (dd, 2H, J1=J2=8.1), 3.20-3.43 (m, 2H), 3.60 (s, 3H), 4.30-4.38 (m, 1H), 6.17-6.23 (m, 1H), 6.45-6.55 (m, 1H), 6.56-6.60 (m, 1H), 6.62-6.74 (m, 2H), 6.78-6.88 (m, 1H), 6.94-7.15 (m, 3H); HPLC-MS calcd. for C28H36FN3O3 (M+H+) 482.3, found 482.5.

Workup

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

Sources & evidence

ORD record
ord-53b0cdfb37484132a08441752c8598d9
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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