Sodium Hydroxide → 4-({[4-(dipropylamino)butyl]amino}methyl)-N,N-bis(1H-imidazol-2-ylmethyl)benzamide

HRID 68629Notes

Reaction equation

[CH2:1]([N:4]([CH2:48][CH2:49][CH3:50])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:47]=[CH:46][C:14]([C:15]([N:17]([CH2:32][C:33]2[N:34](COCC[Si](C)(C)C)[CH:35]=[CH:36][N:37]=2)[CH2:18][C:19]2[N:20](COCC[Si](C)(C)C)[CH:21]=[CH:22][N:23]=2)=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[OH-].[Na+]>CO.Cl>[CH2:48]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:17]([CH2:32][C:33]2[NH:34][CH:35]=[CH:36][N:37]=2)[CH2:18][C:19]2[NH:23][CH:22]=[CH:21][N:20]=2)=[O:16])=[CH:46][CH:47]=1)[CH2:49][CH3:50]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the compound 9 in methanol (2 mL), concentrated hydrochloric acid (2 mL) was added. The reaction mixture was stirred at 80° C. for 5 hours. The reaction mixture was added by an aqueous 5N sodium hydroxide solution and then extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=80:10:1→80:20:4) to obtain the title compound (21 mg) having the following physical properties.

Workup

extractionextracted with dichloromethane
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=80:10:1→80:20:4)

Sources & evidence

ORD record: ord-9db2b9dda76f4443b2bd526b2843f450
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822459B2

Reaction notes

Loading…