홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Diisopropylethylamine → 7-(3,4-dichlorophenyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline

HRID 2383399
노트
인쇄 미리보기

반응식

HRID 2383399 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][C:17]3[CH:16]=[N:15][C:14]4[N:19](CC5C=CC(OC)=CC=5)[N:20]=[CH:21][C:13]=4[C:12]=3[C:11]3[CH:31]=[CH:32][CH:33]=[CH:34][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C(C2C3C(=CC=CC=3)C(=O)/C(=C/N(C)C)/C2)C=CC=1Cl.Cl.COC1C=CC(CN2C(N)=CC=N2)=CC=1.CCN(C(C)C)C(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][C:17]3[CH:16]=[N:15][C:14]4[NH:19][N:20]=[CH:21][C:13]=4[C:12]=3[C:11]3[CH:31]=[CH:32][CH:33]=[CH:34][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 5914006(2E)-4-(3,4-dichlorophenyl)-2-(dimethylaminomethylidene)-3,4-dihydronaphthalen-1-oneHCID 429375131-(4-methoxybenzyl)-1H-pyrazol-5-amine hydrochlorideHCID 674251267-(3,4-dichlorophenyl)-3-(4-methoxybenzyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline

생성물 1

HCID 594907547-(3,4-dichlorophenyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline
수율 53%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
110 °C

실험 절차

Synthesis of 7-(3,4-dichlorophenyl)-3-(4-methoxybenzyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline. To the mixture of (E)-4-(3,4-dichlorophenyl)-2-((dimethylamino)methylene)-3,4-dihydronaphthalen-1(2H)-one (0.20 g, 0.58 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine hydrochloride (0.14 g, 0.58 mmol) was added glacial acetic acid (5 mL) and Hunig's Base (0.4 mL). The mixture was heated at 110° C. for 1 hour, then transferred to microwave vial and heated at 220° C. for 90 minutes. The reaction mixture was evaporated and dissolved in dichloromethane (100 mL), washed with water (30 mL), brine (30 mL), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash column chromatography (SiO2, 10% EtOAc in hexane) to give the pure desired product as a brown solid (0.15 g, 53%). M.p.=76-78° C.; 1H NMR (CDCl3, 400 MHz) δ 9.53 (d, J=8 Hz, 1H), 8.32 (s, 1H), 8.02 (s, 1H), 7.54 (t, J=6.8 Hz, 1H), 7.45 (t, J=8 Hz, 1H), 7.35-7.26 (m, 4H), 7.06 (d, J=8 Hz, 1H), 6.96 (d, J=8 HZ, 1H), 6.843 (d, J=7.2 Hz, 2H), 4.28 (t, J=8 Hz, 1H), 4.17 (s, 2H), 3.77 (s, 3H), 3.29-3.26 (m, 2H); LCMS: 486 [M+1].

후처리

  1. temperatureheated at 220° C. for 90 minutes
  2. customThe reaction mixture was evaporated
  3. dissolutiondissolved in dichloromethane (100 mL)
  4. washwashed with water (30 mL), brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe crude was purified by flash column chromatography (SiO2, 10% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-47f87d4dce054707b62a9d324c10ffa0
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263610B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트