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

HRID 607610노트

반응식

HRID 607610 반응식
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][NH2:19])=[N:14][CH:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:20]1[C:29]2[C:24](=[CH:25][C:26]([C:30]3([CH:33]=O)[CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C.C(O)(=O)C>[F:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][C:15]3[N:16]([C:33]([C:30]4([C:26]5[CH:25]=[C:24]6[C:29](=[CH:28][CH:27]=5)[N:20]=[CH:21][CH:22]=[CH:23]6)[CH2:32][CH2:31]4)=[N:19][N:18]=3)[N:17]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

6

반응물 3

HCID 12217721Iodo benzene diacetateHCID 592162771-Quinolin-6-ylcyclopropanecarbaldehydeHCID 59216321Methyl 2-fluoro-4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate

생성물 1

HCID 59216283Methyl 2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoate수율 53.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

A mixture of methyl 2-fluoro-4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate (0.17 g, 0.64 mmol) and 1-quinolin-6-ylcyclopropanecarbaldehyde (0.13 g, 0.64 mmol) in ethanol (10 mL) and acetic acid (1 mL) was stirred at RT for 2 h. The mixture was concentrated. The residue was dissolved in methylene chloride (5 mL). To the solution was added iodobenzene diacetate (230 mg, 0.71 mmol) with stirring. The mixture was stirred at RT for 2 h then concentrated. The residue was flash chromatographed on a silica gel column to give the desired product (150 mg). Analytical LCMS: (M+H)+=441.0.

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in methylene chloride (5 mL)
  3. stirringwith stirring
  4. stirringThe mixture was stirred at RT for 2 h
  5. concentrationthen concentrated
  6. customchromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-92681352d4a847768657828be5ad16a2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915408B2

반응 노트

불러오는 중…