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 1881747Notes

Reaction equation

HRID 1881747 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-38ded34384b94830ac7f22576361ea20
Source dataset
uspto-grants-2012_11
Patent number
US08318931B2

Reaction notes

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