반응 #1107103

반응 방정식

sodium cyanoborohydride

3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde

1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-ylamine

acetic acid

→

4H-benzo[1,4]oxazin-3-one

수율 167.6%

용매

1,2-dichloroethane

methanol

반응 조건

후처리

1. 1
   추출the reaction mixture is extracted with dichloromethane (3×20 mL)
2. 2
   건조The combined organic layers are dried over sodium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to give a residue that
6. 6
   기타is purified by preparative HPLC

실험 절차

3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (354 mg, 2.00 mmol, 1.0 eq) is added at room temperature to a stirred solution of 1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-ylamine (0.65 g, 2.00 mmol, 1.0 eq) in 1,2-dichloroethane (4 mL) and methanol (1 mL), followed by acetic acid (0.11 mL, 2.00 mmol, 1.0 eq) and sodium cyanoborohydride (160 mg, 2.6 mmol, 1.4 eq). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and a saturated sodium hydrogen carbonate aqueous solution (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by preparative HPLC to afford 6-({1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amino)-methyl)-4H-benzo[1,4]oxazin-3-one as a white solid (500 mg, 52% yield).

출처