(S)-N-(4-(Oxiran-2-ylmethoxy)phenyl)methanesulfonamide → 4-(4-{2-[(2S)-2-Hydroxy-3-(4-methanesulfonylamino-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid Octylamide

HRID 395997Notes

Reaction equation

HRID 395997 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:27]=[CH:26][C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[O:28]1[CH2:30][C@H:29]1[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:35][CH:34]=1>C(Cl)(Cl)Cl.CO>[CH2:18]([NH:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][CH2:30][C@H:29]([OH:28])[CH2:31][O:32][C:33]3[CH:34]=[CH:35][C:36]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:37][CH:38]=3)=[CH:27][CH:26]=2)[CH2:10][CH2:11]1)=[O:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 11322479(S)-N-(4-(Oxiran-2-ylmethoxy)phenyl)methanesulfonamideHCID 181736624-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide

Product 1

HCID 101892484-(4-{2-[(2S)-2-Hydroxy-3-(4-methanesulfonylamino-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid OctylamideYield 12.1%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide (0.245 g, 0.58 mmol) was reacted with N-{4-[(2S)oxiranylmethoxy]phenyl}methanesulfonamide (0.13 g, 0.53 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.04 g, 0.064 mmol).

Sources & evidence

ORD record
ord-227ae8718c594e1da2511698c2342d5f
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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