1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-{1-[2-(methoxy)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178421Notes

Reaction equation

HRID 1178421 reaction equation
CCN=C=NCCCN(C)C.ClC1SC2NC(C(NC3CC4C(=CC=CC=4)N(CC(O)CO)C3=O)=O)=CC=2C=1.[Cl:40][C:41]1[S:70][C:44]2[NH:45][C:46]([C:48]([NH:50][CH:51]3[CH2:60][C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[N:53]([CH2:61][C@@H:62]4CO[C:64](C)(C)[O:63]4)[C:52]3=[O:69])=[O:49])=[CH:47][C:43]=2[CH:42]=1>C(Cl)Cl>[Cl:40][C:41]1[S:70][C:44]2[NH:45][C:46]([C:48]([NH:50][CH:51]3[CH2:60][C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[N:53]([CH2:61][CH2:62][O:63][CH3:64])[C:52]3=[O:69])=[O:49])=[CH:47][C:43]=2[CH:42]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 103895012-Chloro-N-[1-(2,2-dimethyl-1,3-dioxolan-4(R)-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3(R,S)-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

Product 1

HCID 102506062-Chloro-N-{1-[2-(methoxy)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDCI (225 mg, 1.17 mmol) was added to a suspension of 5-carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (Method 9, 234 mg, 1.06 mmol) and 3-amino-1-(2-methoxyethyl)-3,4-dihydroquinolin-2(1H)-one (Method 12; 215 mg, 1.06 mmol) in DCM (20 mL) and the reaction stirred for 18 hours. The reaction was evaporated and the residue was partitioned between DCM:MeOH (9:1) (100 mL) and water (25 mL). The organic layer was then separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:MeOH (9:1)) to afford the title compound (180 mg, 42%) as a yellow solid.

Workup

  1. customThe reaction was evaporated
  2. customthe residue was partitioned between DCM:MeOH (9:1) (100 mL) and water (25 mL)
  3. customThe organic layer was then separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (DCM to DCM:MeOH (9:1))

Sources & evidence

ORD record
ord-dab8c8dd426a43688454168e38c2c3e4
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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