Cyclohexanone, 4-(dipropylamino)- → N,N-bis({1-[(dimethylamino)sulfonyl]-1H-imidazol-2-yl}methyl)-2-[4-(dipropylamino)cyclohexyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxamide

HRID 1920135Notes

Reaction equation

HRID 1920135 reaction equation
[CH3:1][N:2]([CH3:37])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:25][C:26]1[N:27]([S:31]([N:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])[CH:28]=[CH:29][N:30]=1)[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH2:21][NH:20][CH2:19][CH2:18]2)=[O:14])(=[O:5])=[O:4].[CH2:38]([N:41]([CH2:49][CH2:50][CH3:51])[CH:42]1[CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]1)[CH2:39][CH3:40]>>[CH3:35][N:34]([CH3:36])[S:31]([N:27]1[CH:28]=[CH:29][N:30]=[C:26]1[CH2:25][N:12]([CH2:11][C:7]1[N:6]([S:3]([N:2]([CH3:37])[CH3:1])(=[O:4])=[O:5])[CH:10]=[CH:9][N:8]=1)[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH2:21][N:20]([CH:45]1[CH2:46][CH2:47][CH:42]([N:41]([CH2:49][CH2:50][CH3:51])[CH2:38][CH2:39][CH3:40])[CH2:43][CH2:44]1)[CH2:19][CH2:18]2)=[O:14])(=[O:33])=[O:32]

Participants

3

Reactant 2

HCID 10997953Cyclohexanone, 4-(dipropylamino)-HCID 67500558N,N-bis({1-[(dimethylamino)sulfonyl]-1H-imidazol-2-yl}methyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide

Product 1

HCID 67502292N,N-bis({1-[(dimethylamino)sulfonyl]-1H-imidazol-2-yl}methyl)-2-[4-(dipropylamino)cyclohexyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxamideYield 75.2%

Procedure

The same operation as in Example 2 was performed, except for using the compound (150 mg) obtained in Example 31 and 4-(dipropylamino)cyclohexanone (269 mg), and then the obtained crude product was purified by silica gel chromatography (dichrolomethane:methanol:28% aqueous ammonia=1:0:0→80:10:1) to obtain the title compound (150 mg) having the following physical properties.

Workup

  1. customthe obtained crude product
  2. customwas purified by silica gel chromatography (dichrolomethane:methanol:28% aqueous ammonia=1:0:0→80:10:1)

Sources & evidence

ORD record
ord-8bc9829ebd81428ba1347c1d1e46150e
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

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