(2S)-2-[(4-fluorophenoxy)methyl]oxirane → 4-(4-{2-[(2S)-3-(4-Fluoro-phenoxy)-2-hydroxy-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid Octylamide

HRID 1281485Notes

Reaction equation

HRID 1281485 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.[F:31][C:32]1[CH:42]=[CH:41][C:35]([O:36][CH2:37][C@@H:38]2[CH2:40][O:39]2)=[CH:34][CH:33]=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][CH2:40][C@H:38]([OH:39])[CH2:37][O:36][C:35]3[CH:41]=[CH:42][C:32]([F:31])=[CH:33][CH:34]=3)=[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

3

Reactant 2

HCID 6932898(2S)-2-[(4-fluorophenoxy)methyl]oxiraneHCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 103024774-(4-{2-[(2S)-3-(4-Fluoro-phenoxy)-2-hydroxy-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid OctylamideYield 21%

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.400 g, 0.95 mmol) was reacted with (2S)-2-[(4-fluorophenoxy)methyl]oxirane (0.119 g, 0.713 mmol) according to Procedure G to give the title compound (eluant: 20:1 chloroform-methanol) (0.085 g, 0.15 mmol).

Sources & evidence

ORD record
ord-5023463dcf2d47e58462e16ac0806a70
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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