1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247523Notes

Reaction equation

HRID 1247523 reaction equation
[Cl:1][C:2]1[S:28][C:5]2[NH:6][C:7]([C:9]([NH:11][CH:12]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([CH2:22][CH:23]([OH:26])[CH2:24][OH:25])[C:13]3=[O:27])=[O:10])=[CH:8][C:4]=2[CH:3]=1.[CH:29]1[CH:30]=CC2N(O)N=NC=2[CH:34]=1.CCN=C=NCCCN(C)C.C(CN1C2C(=CC=CC=2)CC(NC(C2NC3SC(Cl)=CC=3C=2)=O)C1=O)(O)=O>CN(C=O)C>[CH3:34][C:29]1([CH3:30])[O:26][CH:23]([CH2:22][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:21][CH:12]([NH:11][C:9]([C:7]3[NH:6][C:5]4[S:28][C:2]([Cl:1])=[CH:3][C:4]=4[CH:8]=3)=[O:10])[C:13]2=[O:27])[CH2:24][O:25]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-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 21906856N-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (Method 9; 243 mg, 1.20 mmol), HOBT (178 mg, 1.32 mmol), anhydrous DMF (10 mL) and finally EDCI (252 mg, 1.32 mmol) were added to 3-amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-3,4-dihydroquinolin-2(1H)-one (Method 2, 330 mg, 1.20 mmol) and the reaction was stirred for 18 h. The reaction was evaporated and the residue was dissolved in EtOAc (100 mL) and washed with 1M aqueous HCl (50 mL) and the organic layer was further washed with sat. aqueous NaHCO3 (30 mL) and brine (30 mL). The organic layer was then separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (EtOAc:hexanes 1:2) to afford the title compound (382 mg, 69%) as a white solid.

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (100 mL)
  3. washwashed with 1M aqueous HCl (50 mL)
  4. washthe organic layer was further washed with sat. aqueous NaHCO3 (30 mL) and brine (30 mL)
  5. customThe organic layer was then separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (EtOAc:hexanes 1:2)

Sources & evidence

ORD record
ord-80da131a2657466e87de6cab0f3a123d
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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