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 1247514노트

반응식

HRID 1247514 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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 mL) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-6b15385fe3a54cf9b51be33c9f69624a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129249B2

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