Dabco → HCID 66810931, compound

HRID 388803Notes

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

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-2241b330779c43d9a8566a143264ea49
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377964B2

Reaction notes

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