Iodo benzene diacetate → Methyl 4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoate

HRID 607595노트

반응식

HRID 607595 반응식
[NH:1]([C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:7][N:8]=1)[NH2:2].[N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3([CH:32]=O)[CH2:31][CH2:30]3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C.C(O)(=O)C>[N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3([C:32]4[N:4]5[N:5]=[C:6]([C:9]6[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=6)[CH:7]=[N:8][C:3]5=[N:1][N:2]=4)[CH2:31][CH2:30]3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 12217721Iodo benzene diacetateHCID 592162771-Quinolin-6-ylcyclopropanecarbaldehydeHCID 59216328Methyl 4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate

생성물 1

HCID 59216329Methyl 4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoate수율 60.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

A mixture of methyl 4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate (115 mg, 0.000469 mol) and 1-quinolin-6-ylcyclopropanecarbaldehyde (92 mg, 0.00047 mol) in ethanol (2 mL) and acetic acid (0.5 mL) was stirred at RT for 6 h. The volatiles were removed under reduced pressure. The residue was dried under high vacuum, and then dissolved in methylene chloride (6 mL). To the solution was added iodobenzene diacetate (180 mg, 0.00056 mol). The reaction mixture was stirred at RT overnight. The solvent was evaporated and the residue was flash chromatographed on a silica gel column to afford the desired product (120 mg, 60%). Analytical LCMS: (M+H)+=423.3.

후처리

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue was dried under high vacuum
  3. dissolutiondissolved in methylene chloride (6 mL)
  4. stirringThe reaction mixture was stirred at RT overnight
  5. customThe solvent was evaporated
  6. customchromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-811d76031e7a41b6afdc1b3ba02ab780
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915408B2

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