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1,2-Dichloroethane → N'-(4-(2-(2,2-Dimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-methoxyphenyl)malonamide

HRID 418675
ノート
印刷プレビュー

反応式

HRID 418675 の反応式
N[C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]([NH:18][N:19]([CH3:21])[CH3:20])=[O:17])[S:15][C:8]=23)=[C:4]([F:24])[CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:39])[CH2:35][C:36]([OH:38])=O.C(Cl)CCl.C[N:45](C=O)C>CCOC(C)=O>[CH3:20][N:19]([CH3:21])[NH:18][C:16]([C:14]1[S:15][C:8]2[C:9](=[N:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:22]=[CH:23][C:2]([N:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH3:25])[C:34](=[O:39])[CH2:35][C:36]([NH2:45])=[O:38])=[CH:3][C:4]=2[F:24])[CH:13]=1)=[O:17]
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 4

HCID 111,2-Dichloroethane2 回HCID 6228DimethylformamideHCID 12664594N-(2-Methoxy-phenyl)-malonamic acid2 回HCID 587902227-(4-amino-2-fluorophenoxy)-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide

生成物 1

HCID 66649285N'-(4-(2-(2,2-Dimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-methoxyphenyl)malonamide
収率 67%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 7-(4-amino-2-fluorophenoxy)-N′,N′-dimethylthieno[3,2-b]pyridine-2-carbohydrazide 239 (200 mg, 0.578 mmol), 3-(2-methoxyphenylamino)-3-oxopropanoic acid 27 (195 mg, 0.693 mmol), and EDC (230 mg, 0.693 mmol) in DMF (8.3 mL) was stirred overnight at room temperature. More 27 (195 mg, 0.693 mmol) and EDC (230 mg, 0.693 mmol) were added and the mixture stirred 6 h more. The crude was diluted with EtOAc, extracted with water, over with anhydrous Na2SO4, and concentrated under reduced pressure. The residue was re dissolved in MeOH and purified twice by flash chromatography (DCM/MeOH 9:1) affording 236 (207 mg, 0.385 mmol, 67% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.60 (s, 1H), 9.94 (s, 0.5H), 9.63 (s, 1H), 9.49 (s, 0.5H), 8.57 (dd, J=5.5 Hz, J=7.2 Hz, 1H), 8.26 (m, 1H), 8.07 (d, J=7.4 Hz, 1H), 7.88 (d, J=12.9 Hz, 1H), 7.54-7.43 (m, 2H), 7.07 (m, 2H), 6.91 (m, 1H), 6.73 (m, 1H), 3.86 (s, 3H), 3.65 (s, 2H), 2.63 (s, 3H), 2.61 (s, 3H). MS (m/z): (M+1) 538.0 (100%).

後処理

  1. extractionextracted with water, over with anhydrous Na2SO4
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was re dissolved in MeOH
  4. custompurified twice by flash chromatography (DCM/MeOH 9:1)

出典と根拠

ORDレコード
ord-71b0c3bcae564d468196cbbd766c5524
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093264B2

反応ノート

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