1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-chloro-N-(1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247512Notes

Reaction equation

HRID 1247512 reaction equation
CCN=C=NCCCN(C)C.[C:12]([C:15]1[NH:19][C:18]2[S:20][C:21]([Cl:23])=[CH:22][C:17]=2[CH:16]=1)([OH:14])=O.[NH2:24][CH:25]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH2:35][CH2:36][S:37][CH3:38])[C:26]1=[O:39].ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[Cl:23][C:21]1[S:20][C:18]2[NH:19][C:15]([C:12]([NH:24][CH:25]3[CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][S:37][CH3:38])[C:26]3=[O:39])=[O:14])=[CH:16][C:17]=2[CH:22]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 104428202-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acidHCID 219068283-amino-1-[2-(methylthio)ethyl]-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 100477312-chloro-N-(1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDCI (915 mg, 4.77 mmol) was added to a suspension of 5-Carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (801 mg, 3.97 mmol), 3-amino-1-[2-(methylthio)ethyl]-3,4-dihydroquinolin-2(1H)-one (Method 16; 1.40 g, 3.97 mmol) and 1-hydroxybenzotriazole (537 mg, 3.97 mmol) in DCM (60 mL) and the reaction stirred for 18 hours. The reaction was evaporated and the residue was partitioned between DCM (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:EtOAc (9:1)) to afford the title compound (660 mg, 40%) as a white solid.

Workup

  1. customThe reaction was evaporated
  2. customthe residue was partitioned between DCM (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:EtOAc (9:1))

Sources & evidence

ORD record
ord-747fd3c5ef6b46afb5292bab55e4da38
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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