Dichloromethane → 2,3-Dichloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-4H-thieno[3,2-b]pyrrole-5-carboxamide

HRID 1178431ノート

反応式

HRID 1178431 の反応式
[Cl:1][C:2]1[S:26][C:5]2NC(C(NC3CC4C(=CC=CC=4)N(CCO)C3=O)=O)=C[C:4]=2[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.ClC1SC2[NH:53][C:54]([C:56]([NH:58][CH:59]3[CH2:68][C:67]4[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=4)[N:61]([CH2:69][C:70]([O:72][CH3:73])=[O:71])[C:60]3=[O:74])=[O:57])=[CH:55]C=2C=1.C(Cl)[Cl:77]>O>[Cl:1][C:2]1[S:26][C:5]2[CH:55]=[C:54]([C:56]([NH:58][CH:59]3[CH2:68][C:67]4[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=4)[N:61]([CH2:69][C:70]([O:72][CH3:73])=[O:71])[C:60]3=[O:74])=[O:57])[NH:53][C:4]=2[C:3]=1[Cl:77]

参加物

7

反応物 5

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 100020612-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 104304502-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

生成物 1

HCID 104790032,3-Dichloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-4H-thieno[3,2-b]pyrrole-5-carboxamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-Carboxy-2,3-dichloro-4H-thieno[3,2-b]pyrrole (Method 8; 595 mg, 2.52 mmol), HOBt (340 mg, 2.52 mmol), DCM (100 μL) and finally EDCI (483 mg, 2.52 mmol) were added to methyl (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate (Method 1, 590 mg, 2.52 mmol) and the reaction was stirred for 18 hours The reaction was then diluted with water (50 mL) and stirred vigorously for 30 min. The resultant precipitate was filtered and washed with Et2O (2×20 mL). After filtration the resultant solid was then triturated with refluxing Et2O (25 mL) and after cooling the title compound (528 mg, 46%) was collected again by filtration as a white solid.

後処理

  1. stirringstirred vigorously for 30 min
  2. filtrationThe resultant precipitate was filtered
  3. washwashed with Et2O (2×20 mL)
  4. filtrationAfter filtration the resultant solid
  5. customwas then triturated with refluxing Et2O (25 mL)
  6. temperatureafter cooling the title compound (528 mg, 46%)
  7. filtrationwas collected again by filtration as a white solid

出典と根拠

ORDレコード
ord-582bdc6fe39c4f8e9af0f5a6ed38ecce
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

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