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

HRID 1899938ノート

反応式

HRID 1899938 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b31cfd9379b946089491fbf01a0142c2
出典データセット
uspto-grants-1996_11
特許番号
US05574038

反応ノート

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