Ethyl Beta-Carboline-3-Carboxylate → 3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

HRID 355817

반응식

HRID 355817 반응식
[O-]CC.[Na+].[Na].[CH:6]1([C:9](=[NH:11])[NH2:10])[CH2:8][CH2:7]1.C([O:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=3)=O)C>O.C(O)C.C1(C)C=CC=CC=1>[CH:6]1([C:9]2[N:10]=[C:15]([C:17]3[N:18]=[CH:19][C:20]4[NH:21][C:22]5[C:27]([C:28]=4[CH:29]=3)=[CH:26][CH:25]=[CH:24][CH:23]=5)[O:14][N:11]=2)[CH2:8][CH2:7]1

참가 물질

8

반응물 4

HCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 431751CyclopropanecarboximidamideHCID 2723922Sodium ethoxideHCID 5360545Sodium

생성물 1

HCID 189407253-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline수율 52%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a solution of sodium ethoxide, prepared from sodium metal (0.6 g, 26 mmol) and anhydrous ethanol (50 mL), cyclopropylmethanimidamide (1.67 g, 16 mmol) and 9H-β-carboline-3-carboxylic acid ethyl ester (2.0 g, 8.0 mmol) were added. Toluene (50 mL) was added and the resulting mixture was heated to 120°-130° C. The ethanol and water formed during the reaction were removed by azeotropic distillation. The reaction was complete after 30 min. The solid was filtered from the reaction mixture, washed with water and dried. This afforded the title compound (1.15 g, 52%) as an yellow solid. M.p. 256°-257° C.

후처리

  1. additionwere added
  2. temperaturethe resulting mixture was heated to 120°-130° C
  3. customwere removed by azeotropic distillation
  4. filtrationThe solid was filtered from the reaction mixture
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-a5fa28fb02984bcaa1055039dc7cd15f
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834482

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