7-BROMO-1,3,4,5-TETRAHYDRO-2H-PYRIDO[2,3-E][1,4]DIAZEPIN-2-ONE synthesis
- Product Name:7-BROMO-1,3,4,5-TETRAHYDRO-2H-PYRIDO[2,3-E][1,4]DIAZEPIN-2-ONE
- CAS Number:709650-05-5
- Molecular formula:C8H8BrN3O
- Molecular Weight:242.07
709650-04-4
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Yield:709650-05-5 72%
Reaction Conditions:
with sodium hydride in dimethyl sulfoxide at 20; for 27 h;
Steps:
XVII.b; XVIII.b; 54.b b) 7-BROMO-1, 3, 4, 5-TETRAHYDRO-PYRIDO [2, 3-E] [1, 4] diazepin-2-one; Scheme XVII
A solution of [ (2-amino-5-bromo-pyridin-3-ylmethyl) amino] acetic acid ethyl ester (1.79 g, 6.21 mmol) in DMSO (70 mL) was treated with NaH (60% dispersion in mineral oil, 0.25 g, 6.2 mmol). After stirring at room temperature for 27 h, the mixture was diluted with H20 (300 mL), and extracted then with EtOAc (4 x 150 mL). The combined organic layers were washed with H20 (3 x 50 mL) and brine (50 mL), dried over NA2SO4, filtered and the solvent was removed in vacuo to give the title compound (1.09 g, 72%) as an off- WHITE SOLID : IH NMR (300 MHz, CDCl3) 8 8.26 (d, J= 2. 1 Hz, 1H), 8.17 (s, 1H), 7.54 (d, J = 1. 9 Hz, 1H), 4.03 (s, 2H), 3.93 (s, 2H), 1.85 (br s, 1H); MS (ESI) 777/E 242 (M + H) +.
References:
WO2004/52890,2004,A1 Location in patent:Page 52-53; 105
5345-47-1
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