(1H-benzimidazol-2-yl)(piperidin-4-yl)amine → 1-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

HRID 323308Notes

Reaction equation

HRID 323308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)([CH2:12][CH2:13][CH2:14]S(C)(=O)=O)[C:8]1=[O:27].[NH:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[C:36]1[NH:44][CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][CH2:14][N:48]2[CH2:47][CH2:46][CH:45]([NH:44][C:36]3[NH:35][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[N:37]=3)[CH2:50][CH2:49]2)([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:8]1=[O:27]

Participants

3

Reactant 2

HCID 15718789(1H-benzimidazol-2-yl)(piperidin-4-yl)amineHCID 183334941-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonylpropyl)-2-oxopyrrolidine

Product 1

HCID 98954571-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

Procedure

Prepare by the method of Example 6.6 using 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonylpropyl)-2-oxopyrrolidine (0.32 g, 0.63 mmol) and (1H-benzimidazol-2-yl)(piperidin-4-yl)amine (0.30 g, 0.63 mmol). Purify by chromatography on silica gel eluting with 2% triethylamine/30% ethyl acetate/methanol to give the title compound: Rf=0.55 (silica gel, 2% triethylamine/methanol).

Workup

  1. customPurify by chromatography on silica gel eluting with 2% triethylamine/30% ethyl acetate/methanol

Sources & evidence

ORD record
ord-c5476db5e48344de8f49c4d90e74774b
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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