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

HRID 2383399
ノート
印刷プレビュー

反応式

HRID 2383399 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
110 °C

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-47f87d4dce054707b62a9d324c10ffa0
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263610B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート