Ethylamine → HCID 86697770, compound

HRID 2279831Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:9]([O:11]CC)=O)=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.[CH2:14]([NH2:16])[CH3:15].C1COCC1>C(O)C>[NH2:1][C:2]1[C:3]([C:9]([NH:16][CH2:14][CH3:15])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred suspension of ethyl 3-amino-6-bromopyridine-2-carboxylate (5 g, 20.3 mmol) in ethanol (40 mL) in a steel bomb was treated with a 2M solution of ethylamine in THF (220 mL, 440 mmol) and heated to 120° C. for 2 days. The reaction mixture was cooled to RT, the solvents were evaporated under reduced pressure and the residue was purified by column chromatography (SiO2, 0.5% methanol in dichloromethane) to give 3.5 g (70%) of the required material as white solid 1H NMR (400 MHz, CDCl3) δ 7.77 (brs, 1H), 7.21 (d, J=8.8 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 5.99 (brs, 2H), 3.4 (q, J=7.2 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H).

Workup

temperatureThe reaction mixture was cooled to RT
customthe solvents were evaporated under reduced pressure
customthe residue was purified by column chromatography (SiO2, 0.5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-6e67024dfa084405b087928f514fc002
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133224B2

Reaction notes

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