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 2067720Notes

Reaction equation

HRID 2067720 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-3bd303945e9f41d5b7eab6d95fdee195
Source dataset
uspto-grants-2012_10
Patent number
US08293896B2

Reaction notes

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