Benzylamine → 6-Amino-4-benzylamino-2-furan-2-yl-nicotinonitrile

HRID 1356022

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOC>[NH2:1][C:2]1[CH:3]=[C:4]([NH:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 250 mg (0.75 mmol) trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester in 10 ml DME was added 0.82 ml (7.56 mmol) benzylamine and the mixture heated at 80° C. for 72 hours. The reaction mixture was then cooled to room temperature and partitioned between dichloromethane and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether/hexane to afford 79 mg (38%) 6-amino-4-benzylamino-2-furan-2-yl-nicotinonitrile as a white crystalline solid. ES-MS m/e (%): 291 (M+H+, 100).

Workup

temperatureThe reaction mixture was then cooled to room temperature
custompartitioned between dichloromethane and water
customThe phases were separated
dry with materialthe organic phase dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was triturated in ether/hexane

Sources & evidence

ORD record: ord-43d2dd40bb0f4550a44a7c264d7c75bc
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Linked notes

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