Dabco → HCID 66810931, compound
Reaction equation
Cl.[C:2]([C:6]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([C:15]([OH:17])=O)[C:8]=2[N:7]=1)([CH3:5])([CH3:4])[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][CH:40]([CH2:43][NH2:44])[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31].N12CCN(CC1)CC2>CN(C)C=O.O.C(OCC)(=O)C>[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][CH:40]([CH2:43][NH:44][C:15]([C:14]2[C:8]3[N:7]=[C:6]([C:2]([CH3:3])([CH3:4])[CH3:5])[NH:10][C:9]=3[CH:11]=[CH:12][CH:13]=2)=[O:17])[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-tert-butyl-1H-benzoimidazole-4-carboxylic acid hydrochloride (1.11 g, 4.37 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added 1,1′-carbonyldiimidazole (0.77 g, 4.75 mmol). The solution was stirred at 50° C. for 2 h, then 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (0.94 g, 4.39 mmol) was added, followed by 1,4-diazabicyclo[2,2,2]octane (1.46 g, 13 mmol). The solution was stirred at 50° C. for 16 h, allowed to cool and diluted with water (20 mL) and ethyl acetate (60 mL). The aqueous layer was removed, the organic layer washed with water (20 mL), dried over sodium sulfate and concentrated in vacuo to afford the title intermediate (1.32 g, 3.18 mmol, 73%) which was used without further purification. (m/z): [M+H]+ calcd for C23H34N4O3 415.27. found 415.5.
Workup
- stirringThe solution was stirred at 50° C. for 16 h
- temperatureto cool
- customThe aqueous layer was removed
- washthe organic layer washed with water (20 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e8f9926ea64e43b18e63dc7e5d7d7a4b
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428489B2
Reaction notes
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