Ethanolamine → (S)-N-{3-Cyclohexyl-1-[2-(5-cyano-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamide

HRID 132132Notes

Reaction equation

HRID 132132 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.[C:29]([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][CH2:35][CH2:34]2)#[N:30]>>[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][C:31]([C:29]#[N:30])=[CH:39][CH:38]=3)[CH2:34][CH2:35]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 74374m-Anisoyl chlorideHCID 219076392,3-Dihydro-1H-indole-5-carbonitrileHCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

Product 1

HCID 11237152(S)-N-{3-Cyclohexyl-1-[2-(5-cyano-2,3-dihydro-indol-1-yl)-ethylcarbamoyl]-propyl}-3-methoxy-benzamideYield 20%

Procedure

Following the procedures of Example 3, except using m-anisoyl chloride, (S)-2-amino-4-cyclohexyl-butyric acid, ethanolamine and 5-cyanoindoline as starting materials, the title compound was prepared in 20% 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 0.64-0.77 (m, 2H), 0.97-1.15 (m, 6H), 1.49-1.64 (m, 6H), 1.72-1.84 (m, 1H), 2.84-2.92 (m, 2H), 3.16-3.30 (m, 2H), 3.32-3.51 (m, 4H), 3.77 (s, 3H), 4.49 (dd, 1H, J1=7.4, J2=14.4), 6.24 (d, 1H, J1=8.3), 6.97-7.02 (m, 1H), 7.04-7.07 (m, 1H), 7.09-7.15 (m, 2H), 7.18-7.28 (m, 2H); HPLC-MS calcd. for C29H36N4O3 (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-77f9cafc5aad49ebb41bf360ee33a5a6
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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