2-Chloronicotinonitrile → HCID 58996706, compound

HRID 1035109Notes

Reaction equation

Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#N.[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:24](=O)([O-])O.[K+]>CN(C)C=O>[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:4]2[CH:24]=[CH:8][CH:7]=[CH:6][C:3]=2[C:2]#[N:9])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Chloro-nicotinonitrile (1.0 g, 7.215 mmol) was added to a mixture of [1,4]Diazepane-1-carboxylic acid tert-butyl ester and potassium hydrogencarbonate (0.87 g, 8.66 mmol) in N,N-dimethylformamide (20 mL). The mixture was heated at 90° C. overnight. The reaction mixture was poured onto ice and extracted with dichloromethane. The organic layer was washed with water and brine then dried over magnesium sulfate and filtered. The solvent was removed and the residue was purified by flash column chromatography on silica using ethyl acetate/heptane (50:50) mixture as the mobile phase to give 4-(2-Cyano-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester. 1H-NMR (400 MHz, DMSO-d6) δ 1.25 (d, 27 Hz, 9H), 1.81 (m, 1H), 1.87 (m, 1H), 3.31 (m, 2H), 3.55 (m, 1H), 3.60 (m, 1H), 3.84 (m, 2H), 3.94 (m, 2H), 6.75 (m, 2H), 8.34 (m, 1H).

Workup

additionThe reaction mixture was poured onto ice
extractionextracted with dichloromethane
washThe organic layer was washed with water and brine
dry with materialthen dried over magnesium sulfate
filtrationfiltered
customThe solvent was removed
customthe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record: ord-5982c3bcba6947baaf8d7e8575fc48d6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546374B2

Reaction notes

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