Hydrochloric Acid → 9-Bromo-5-(p-ethoxycarbonylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52502

반응식

HRID 52502 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:36]([O:38][C:39]([C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=1)=[O:40])[CH3:37].Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:45][C:44]3[CH:46]=[CH:47][C:41]([C:39]([O:38][CH2:36][CH3:37])=[O:40])=[CH:42][CH:43]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

생성물 1

HCID 541495519-Bromo-5-(p-ethoxycarbonylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione수율 47.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (340 mg, 1 mmol) and triethylamine (140 μL, 1 mmol) in DMF (5 mL) was added isobutyl chloroformate (130 μL, 0.9 mmol) at -10° C. After being stirred for 15 min, p-ethoxycarbonylaniline (200 mg, 1.2 mmol) was added. The mixture was stirred overnight at room temperature and 0.2N hydrochloric acid was added. The precipitates formed were collected by filtration, washed with water, and dried in vacuo. The crude product was rinsed with methanol-water, and dried in vacuo to give 230 mg of the title compound (46%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (s, 1H), 10.35 (s, 1H), 7.92 (d, 2H, J=9 Hz), 7.70 (d, 1H, J=9 Hz), 7.24 (d, 1H, J=2 Hz), 7.17 (d, 2H, J=9 Hz), 5.16~5.28 (m, 1H), 4.28 (q, 2H, J=7.2 Hz), 3.04 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=16.8 Hz), 2.65 (d, 2H, J=7.6 Hz), 2.10 (dm, 1H, J=13.5 Hz), 1.80~1.97 (m, 1H), 1.31 (t, 3H, J=7.2 Hz).

후처리

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe precipitates formed
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. washThe crude product was rinsed with methanol-water
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-5e08b4103da14cf99867c2324a995dcc
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

연결된 노트

불러오는 중…