4-Pyridinemethanamine → HCID 10177272, compound

HRID 1168222Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1>C(OCC)(=O)C>[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:2]2[C:7]([C:8]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of intermediate 1a (6.00 g, 20 mmol) and 4-pyridinemethanamine (30 mL) is stirred at 150° C. for 16 hours under an argon atmosphere. The cooled mixture is diluted with ethyl acetate (100 mL) and extracted with a saturated aqueous solution of sodium hydrogen carbonate (100 mL), followed by water (4×50 mL) and saturated aqueous sodium chloride (50 mL). The ethyl acetate solution is dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate and recrystallised from 2-propanol—diisopropylether to give the title compound as a colourless crystalline solid, m.p. 152-153° C.

Workup

extractionextracted with a saturated aqueous solution of sodium hydrogen carbonate (100 mL)
dry with materialThe ethyl acetate solution is dried (Na2SO4)
filtrationfiltered
customthe solvent is evaporated off under reduced pressure
customto yield the crude product which
customis purified by column chromatography on silica gel, eluent ethyl acetate
customrecrystallised from 2-propanol—diisopropylether

Sources & evidence

ORD record: ord-41e34fb112e048f79288eccb887ec724
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624174B2

Reaction notes

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