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N'-Hydroxycyclopropanecarboximidamide → Imidazo[1,5-a]quinoxaline

HRID 1736697
ノート
印刷プレビュー

反応式

HRID 1736697 の反応式
CC(C)([O-])C.[K+].C1(C(=NO)N)CC1.C[C:15]1(C)[NH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]2[CH:25]=[N:26][C:27](C(OCC)=O)=[C:16]12>C1COCC1>[CH:25]1[N:17]2[C:18]3[C:23]([N:24]=[CH:15][C:16]2=[CH:27][N:26]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 23665647Potassium tert-butoxideHCID 54175730Ethyl 4,5-Dihydro-4,4-dimethylimidazo[1,5-a]quinoxaline-3-carboxylate

生成物 1

HCID 12658625Imidazo[1,5-a]quinoxaline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Potassium tert-butoxide (1M in THF, 1.95 ml) is added to cyclopropylcarboxamide oxime (0.195 g) in THF (7 ml) at 0°. After 10 min ethyl 4,5-dihydro-4,4-dimethylimidazo[1,5-a]quinoxaline-3-carboxylate (XXXIII, EXAMPLE 94, 0.503 g) is added. The ice bath is removed after stirring for 10 min and the reaction is allowed to slowly warm to 20°-25°. After 2 hr DMF (4 ml) is added. When the reaction had stirred for a total of 7 hr, the solvents are removed under reduced pressure and the residue is partitioned between ethyl acetate and saline. The phases are separated, the organic phase is dried over magnesium sulfate and concentrated to give the title compound; mp 175°-179°; NMR (CDCl3): 1.10, 1.76, 2.18, 3.83, 6.79, 6.85, 7.13, 7.42 and 8.10 δ.

後処理

  1. customThe ice bath is removed
  2. temperatureto slowly warm to 20°-25°
  3. additionAfter 2 hr DMF (4 ml) is added
  4. stirringWhen the reaction had stirred for a total of 7 hr
  5. customthe solvents are removed under reduced pressure
  6. customthe residue is partitioned between ethyl acetate and saline
  7. customThe phases are separated
  8. dry with materialthe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-d3784a4b26f04fabad9ab64d8e9463d0
出典データセット
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05541324

反応ノート

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