4-[(2S)Oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-one → 4-(4-(2-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-ethoxy}-phenylamino)-piperidine-1-carboxylic acidoctylamide

HRID 396051Notes

Reaction equation

HRID 396051 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:31]=[CH:30][C:11]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:20])[CH2:15][CH2:14]2)=[CH:10][CH:9]=1.[O:32]1[CH2:34][C@H:33]1[CH2:35][O:36][C:37]1[C:45]2[NH:44][C:43](=[O:46])[NH:42][C:41]=2[CH:40]=[CH:39][CH:38]=1>C(Cl)(Cl)Cl.CO>[CH2:22]([NH:21][C:19]([N:16]1[CH2:15][CH2:14][CH:13]([NH:12][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][NH:4][CH2:34][C@H:33]([OH:32])[CH2:35][O:36][C:37]3[C:45]4[NH:44][C:43](=[O:46])[NH:42][C:41]=4[CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)[CH2:18][CH2:17]1)=[O:20])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 105124504-[(2S)Oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-oneHCID 699876844-[4-(2-Aminoethoxy)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 101453024-(4-(2-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-ethoxy}-phenylamino)-piperidine-1-carboxylic acidoctylamideYield 19.4%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethoxy)anilino]-N-octyl-1-piperidinecarboxamide formate (0.32 g, 0.733 mmol) was reacted with 4-[(2S)oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-one (0.151 g, 0.732 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.085 g, 0.142 mmol).

Sources & evidence

ORD record
ord-a9379cfb1a1749dea611d3ca35215633
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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