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Triethylamine → 5-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-pentanoic Acid Methyl Ester

HRID 220927
ノート
印刷プレビュー

反応式

HRID 220927 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH3:18])=[O:4].[CH3:19][N:20]1[C:29]2[NH:28][C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[NH:25][CH2:24][C:23]=2[CH:22]=[N:21]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:25]2[CH2:24][C:23]3[CH:22]=[N:21][N:20]([CH3:19])[C:29]=3[NH:28][C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]2=3)=[O:15])=[CH:11][C:10]=1[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 575553514-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic AcidHCID 1357419771-Methyl-1,4,5,10-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepine

生成物 1

HCID 1361283645-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-pentanoic Acid Methyl Ester収率 46%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

WSCD (822 mg, 4.3 mmol) and DMAP (273 mg, 2.2 mmol) were added to a solution of 4-(4-methoxycarbonyl-butyl)-3-methyl-benzoic acid from Example E31 (571 mg, 2.3 mmol) and 3-methyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene from Example E11 (424 mg, 2.1 mmol) in dichloromethane (50 ml) and triethylamine (0.6 ml, 4.3 mmol). The mixture was heated at reflux for 72 h, diluted with dichloromethane, washed with 0.3M KHSO4, saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc to 5% triethyamine: 95% EtOAc) to yield the title compound (424 mg, 46%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 72 h
  3. washwashed with 0.3M KHSO4, saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc to 5% triethyamine: 95% EtOAc)

出典と根拠

ORDレコード
ord-06ad42413b314af7a436b20695891ed7
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

読み込み中…

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