Ammonia → Ethyl 2-amino-6-[(2,2-dimethylpropanoyl)amino]nicotinate

HRID 965787Notes

Reaction equation

[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8](F)[N:7]=1)=[O:4].[NH3:20].O>CC(O)C>[NH2:20][C:8]1[N:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:19])([CH3:18])[CH3:1])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of ethyl 6-[(2,2-dimethylpropanoyl)amino]-2-fluoronicotinate (M. C. Coldwell et al., Bioorg. Med. Chem. Lett., 1995, 39, 5, 1.5 g, 5.59 mmol) in 2-propanol (16 mL) was added 25% aqueous ammonia (4 mL) and the mixture was heated in a sealed tube at 70° C. for 4.5 h. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The separated organic layer was concentrated in vacuo and the residue was chromatographed on a column of silica gel eluting with ethyl acetate/pentane (1:6 to 1:2) to give 810 mg (55%) of the title compound as a white solid.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with ethyl acetate
concentrationThe separated organic layer was concentrated in vacuo
customthe residue was chromatographed on a column of silica gel eluting with ethyl acetate/pentane (1:6 to 1:2)

Sources & evidence

ORD record: ord-85098460e20c44b8ace93eb81d576e84
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951867B2

Reaction notes

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