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 1178431Notes

Reaction equation

HRID 1178431 reaction equation
[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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-582bdc6fe39c4f8e9af0f5a6ed38ecce
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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