Phosgene → 3-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydro-5-[(morpholino)carbonyl]imidazo[1,5-a]quinoxaline

HRID 1378754노트

반응식

HRID 1378754 반응식
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[NH:15][CH2:14][C:13]=34)[N:5]=2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[C:31](Cl)(Cl)=[O:32].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C1COCC1>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]([C:31]([N:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[O:32])[CH2:14][C:13]=34)[N:5]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 6371PhosgeneHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 99937443-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydroimidazo[1,5-a]quinoxaline

생성물 1

HCID 106205233-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydro-5-[(morpholino)carbonyl]imidazo[1,5-a]quinoxaline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a slurry consisting of 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydroimidazo[1,5-a]quinoxaline (XXXIII, EXAMPLE 88, 0.499 g), diisopropylethylamine (0.81 ml) and THF (15 ml) is added phosgene (1.93M in toluene, 1.20 ml). A slight exotherm ensues and the slurry becomes homogeneous. After 10 min, morpholine (0.20 ml) is added. The mixture is stirred for 2 hr and then partitioned between ethyl acetate, water, and saline. The phases are separated and the organic phase is dried over magnesium sulfate and concentrated. The crude product is chromatographed on silica gel (150 ml) eluting with methanol/dichloromethane (2/98). The appropriate fractions are pooled and concentrated to give the product. Recrystallization from dichloromethane and hexane gives the title compound, mp 198.0°-198.5°; MS (m/z) at 392; IR 1662, 1506, 1409, 1277, and 1579 cm-1 ; NMR (CDCl3) 1.24, 1.36, 2.27, 3.33, 3.64, 5.02, 7.21, 7.27, 7.55 and 8.11 δ.

후처리

  1. custompartitioned between ethyl acetate, water, and saline
  2. customThe phases are separated
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica gel (150 ml)
  6. washeluting with methanol/dichloromethane (2/98)
  7. concentrationconcentrated
  8. customto give the product
  9. customRecrystallization from dichloromethane and hexane

출처 및 근거

ORD 기록
ord-f5056a8e854e44248350c5aaeebe7aec
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668282

반응 노트

불러오는 중…