8-[(3-Methyl-2-thienyl)methyl]-2,8-diazaspiro[4.5]decane → 3-(1H-imidazol-2-yl)-2-(1H-imidazol-2-ylmethyl)-1-[4-({8-[(3-methyl-2-thienyl)methyl]-2,8-diazaspiro[4.5]dec-2-yl}methyl)phenyl]propan-1-one

HRID 539397Notes

Reaction equation

HRID 539397 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][N:8]1[CH2:17][CH2:16][C:11]2([CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1.[NH:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH2:23][CH:24]([CH2:35][C:36]1[NH:37][CH:38]=[CH:39][N:40]=1)[C:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)=[O:26]>>[NH:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH2:23][CH:24]([CH2:35][C:36]1[NH:37][CH:38]=[CH:39][N:40]=1)[C:25]([C:27]1[CH:28]=[CH:29][C:30]([CH2:31][N:14]2[CH2:13][CH2:12][C:11]3([CH2:10][CH2:9][N:8]([CH2:7][C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])[CH2:17][CH2:16]3)[CH2:15]2)=[CH:33][CH:34]=1)=[O:26]

Participants

3

Reactant 2

HCID 689590078-[(3-Methyl-2-thienyl)methyl]-2,8-diazaspiro[4.5]decaneHCID 866301014-[3-(1H-imidazol-2-yl)-2-(1H-imidazol-2-ylmethyl)propanoyl]benzaldehyde

Product 1

HCID 576855293-(1H-imidazol-2-yl)-2-(1H-imidazol-2-ylmethyl)-1-[4-({8-[(3-methyl-2-thienyl)methyl]-2,8-diazaspiro[4.5]dec-2-yl}methyl)phenyl]propan-1-oneYield 14.7%

Procedure

Using the compound (64 mg) produced in Example 13 and the compound (54 mg) produced in Example 11, the same operation as in Example 12 was performed. The resulting residue was purified by silica gel chromatography (ethyl acetate:methanol:28% aqueous ammonia=100:10:2) to obtain the title compound (14 mg) having the following physical properties.

Workup

  1. customThe resulting residue was purified by silica gel chromatography (ethyl acetate:methanol:28% aqueous ammonia=100:10:2)

Sources & evidence

ORD record
ord-95a4d0812cce43ecb644fda7af1b105c
Source dataset
uspto-grants-2014_10
Patent number
US08871210B2

Reaction notes

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