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Acetic Anhydride → 1-[2-(2,6-dichloroanilino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]allyl acetate

HRID 562427
ノート
印刷プレビュー

反応式

HRID 562427 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:29])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23]([OH:26])[CH:24]=[CH2:25])=[C:17]([CH3:27])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:28]=1.C(N(CC)CC)C.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[N:11]([CH3:29])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23]([O:26][C:37](=[O:39])[CH3:38])[CH:24]=[CH2:25])=[C:17]([CH3:27])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 110912672-(2,6-Dichloro-phenylamino)-7-(1-hydroxy-allyl)-1,6-dimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

生成物 1

HCID 108743751-[2-(2,6-dichloroanilino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]allyl acetate収率 87%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a 100 mL round bottom flask equipped with a magnetic stir bar was added 2-(2,6-dichloro-phenylamino)-7-(1-hydroxy-allyl)-1,6-dimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one (0.175 g, 0.409 mmol), THF (5 mL), triethylamine (60 μL, 0.43 mmol) and acetic anhydride (1 mL). To the stirring suspension was then added N,N-dimethylaminopyridine (2 mg, 0.016 mmol). The reaction mixture became clear in 1 minute, and TLC analysis indicated that all starting material had been consumed. The reaction mixture was concentrated in vacuo and the residue was further purified by silica gel chromatography, eluting with methanol:dichloromethane (0-10%) to provide acetic acid 1-[2-(2,6-dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]-allyl ester (0.168 g, 87%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6+TFA) δ 11.42 (s, 1H), 7.80-7.76 (m, 4H), 7.57 (t, 1H, J=8.2 Hz), 6.34 (d, 1H, J=6.3 Hz), 6.21-6.13 (m, 1H), 5.41 (d, 1H, J=17.2 Hz), 5.33 (d, 1H, J=10.2 Hz), 4.25 (s, 3H), 2.33 (s, 3H), 2.12 (s, 3H); ESMS (m/z): found, 471.

後処理

  1. customTo a 100 mL round bottom flask equipped with a magnetic stir bar
  2. customhad been consumed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was further purified by silica gel chromatography
  5. washeluting with methanol

出典と根拠

ORDレコード
ord-4c037ba7edb64505bb76cef2b3f74b68
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08067395B2

反応ノート

読み込み中…

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