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

HRID 1899938노트

반응식

HRID 1899938 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-oxadizol-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 (1.93 M 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 chromatographod 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 1.579 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. washeluting with methanol/dichloromethane (2/98)
  6. concentrationconcentrated
  7. customto give the product
  8. customRecrystallization from dichloromethane and hexane

출처 및 근거

ORD 기록
ord-b31cfd9379b946089491fbf01a0142c2
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574038

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