1-Methylpiperazine → HCID 68670557, compound
Reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.Cl.Cl.[N:15]1([C:22]2[CH:23]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]=3)[CH:25]=[CH:26][CH:27]=2)[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.[CH3:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.C([O-])(O)=O.[Na+]>ClCCl>[CH3:33][N:32]1[C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[N:29]=[C:28]1[C:24]1[CH:23]=[C:22]([N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:5]([N:51]3[CH2:52][CH2:53][N:48]([CH3:47])[CH2:49][CH2:50]3)=[O:11])[CH2:17][CH2:16]2)[CH:27]=[CH:26][CH:25]=1Participants
Procedure
To a solution of triphosgene (0.41 g, 0.13 mmol) in dichloromethane (2 mL), was added 2-(3-[1,4]Diazepan-1-ylphenyl)-1-methyl-1H-benzoimidazole dihydrochloride salt (0.14 g, 0.37 mmol) and DIPEA (0.11 mL, 0.66 mmol) in dichloromethane (2 mL). After 15 minutes stirring at room temperature was added a solution of N-methyl-piperazine (0.04 mL, 0.44 mmol) and DIPEA (0.04 mL, 0.22 mmol) in dichloromethane (1.5 mL). The resulting suspension was stirred at room temperature for 10 min. The mixture was poured onto a mixture of saturated NaHCO3 solution (25 mL) and dichloromethane (25 mL), the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a residue that was purified by Preparative HPLC, to obtain 20 mg (13%) of the title compound.
Workup
- stirringThe resulting suspension was stirred at room temperature for 10 min
- dry with materialthe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto afford a residue that
- customwas purified by Preparative HPLC
Sources & evidence
- ORD record
- ord-c5b69694ad3b4c46b44a02b8b3fe0832
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592463B2
Reaction notes
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