8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone → 4-(4-[2-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamide

HRID 396045Notes

Reaction equation

HRID 396045 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:30]=[CH:29][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.C([O:38][C:39]1[CH:40]=[CH:41][C:42]([O:50][CH2:51][C@@H:52]2[CH2:54][O:53]2)=[C:43]2[C:48]=1[NH:47][C:46](=[O:49])[CH2:45][CH2:44]2)C1C=CC=CC=1>C(Cl)(Cl)Cl.CO>[CH2:21]([NH:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][NH:4][CH2:54][C@H:52]([OH:53])[CH2:51][O:50][C:42]3[CH:41]=[CH:40][C:39]([OH:38])=[C:48]4[C:43]=3[CH2:44][CH2:45][C:46](=[O:49])[NH:47]4)=[CH:30][CH:29]=2)[CH2:13][CH2:14]1)=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 233813448-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinoneHCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 102325934-(4-[2-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamideYield 27.1%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.431 g, 1.0 mmol) was reacted with 8-(benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone (0.325 g, 1.0 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.19 g, 0.271 mmol).

Sources & evidence

ORD record
ord-5bb4c5d454d64d348c8c8a3ed85cf84b
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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