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

HRID 1178419Notes

Reaction equation

HRID 1178419 reaction equation
ON1C2C=CC=CC=2N=N1.[Cl:11][C:12]1[S:41][C:15]2[NH:16][C:17]([C:19]([NH:21][CH:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:32][C@H:33]4COC(C)(C)O4)[C:23]3=[O:40])=[O:20])=[CH:18][C:14]=2[CH:13]=1.ClC1S[C:46]2[NH:47][C:48](C(NC3CC4C(=CC=CC=4)N(CC(O)CO)C3=O)=O)=CC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:11][C:12]1[S:41][C:15]2[NH:16][C:17]([C:19]([NH:21][CH:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:32][CH2:33][N:47]([CH3:48])[CH3:46])[C:23]3=[O:40])=[O:20])=[CH:18][C:14]=2[CH:13]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 103442072-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxolan-4(S)-yl)methyl]-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 103646262-Chloro-N-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 56%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-Hydroxybenzotriazole (0.69 g, 0.51 mmol) was added to a solution of 3-amino-1-[2-(dimethylamino)ethyl]-3,4-dihydroquinolin-2(1H)-one (Method 10, 100 mg, 0.427 mmol) in DMF (3 mL) followed by 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (Method 9, 86 mg, 0.42 mmol) and EDCI (0.98 g, 0.51 mmol). The reaction was diluted with EtOAc (40 mL) and sat. aqueous NaHCO3 (20 mL) and the separated organic layer was dried (MgSO4), filtered and evaporated to dryness. Purification by column chromatography (MeOH:DCM 1:9) afforded the title compound (70 mg, 56%) as a yellow solid.

Workup

  1. dry with materialthe separated organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customPurification by column chromatography (MeOH:DCM 1:9)

Sources & evidence

ORD record
ord-a02d7889a50d4ac3989014fab87f1eab
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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