Ethylamine → HCID 60631615, compound
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH2:11]([NH2:13])[CH3:12]>>[CH2:11]([NH:13][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1)[CH3:12]Participants
Procedure
Using analogous procedures to those described in the portion of Note [9] immediately above that is concerned with the preparation of starting materials, 5-bromo-2-nitropyridine was reacted with ethylamine to give 5-ethylamino-2-nitropyridine in 97% yield; 1H NMR: (DMSOd6) 1.96 (t, 3H), 3.21 (m, 2H), 7.05 (m, 1H), 7.4 (br s, 1H), 7.87 (m, 1H), 8.12 (m, 1H); Mass Spectrum: M+H+ 168; which in turn was converted into 5-(N-tert-butoxycarbonyl-N-ethylamino)-2-nitropyridine in 81% yield; 1H NMR: (CDCl3) 1.27 (t, 3H), 1.5 (s, 9H), 3.82 (m, 2H), 7.94 (m, 1H), 8.24 (m, 1H), 8.54 (m, 1H); Mass Spectrum: M+H+ 268; which in turn was converted into 2-amino-5-(N-tert-butoxycarbonyl-N-ethylamino)pyridine in 59% yield; 1H NMR: (CDCl3) 1.12 (t, 3H), 1.4 (br s, 9H), 3.58 (q, 2H), 6.48 (d, 1H), 7.24 (m, 1H), 7.89 (m, 1H); Mass Spectrum: M+H+ 238; and which in turn was converted into N-[5-(N-tert-butoxycarbonyl-N-ethylamino)pyridin-2-yl]-2-[4-(6,7-dimethoxyquinazolin-4-yloxy) phenyl]acetamide; Mass Spectrum: M+H+ 560.
Sources & evidence
- ORD record
- ord-26ee5b371c414cd0b2cac90d08dfd702
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153643B2
Reaction notes
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