2-(Benzyloxy)-5-(2-oxiranyl)benzamide → 4-(4-{2-[2-(3-Carbamoyl-4-hydroxy-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid Octylamide

HRID 395982Notes

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:47]=[CH:46][C:45]([CH:48]2[CH2:50][O:49]2)=[CH:44][C:40]=1[C:41]([NH2:43])=[O:42])C1C=CC=CC=1>>[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][CH2:50][CH:48]([C:45]3[CH:46]=[CH:47][C:39]([OH:38])=[C:40]([C:41](=[O:42])[NH2:43])[CH:44]=3)[OH:49])=[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

Reactant 2

HCID 99035062-(Benzyloxy)-5-(2-oxiranyl)benzamide

HCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 699856154-(4-{2-[2-(3-Carbamoyl-4-hydroxy-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid OctylamideYield 23.2%

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.50 g, 1.18 mmol) was reacted with 2-(benzyloxy)-5-(2-oxiranyl)benzamide (0.255 g, 0.95 mmol) according to Procedure G to give the title compound (eluant: 20:1 chloroform-methanol) (0.143 g, 0.22 mmol).

Sources & evidence

ORD record: ord-e16e0e06b34a4ee7b64d07cfe9018baa
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605618B2

Reaction notes

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