Dimethylformamide → 2-Chloro-N-{1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247501Notes

Reaction equation

HRID 1247501 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]([NH:22][C:23]([C:25]2[NH:29][C:28]3[S:30][C:31]([Cl:33])=[CH:32][C:27]=3[CH:26]=2)=[O:24])[C:13]1=[O:34])(O)=[O:9].CCN=C=NCCCN(C)C.CN(C=O)C>CN(C)C1C=CN=CC=1.C1COCC1.O>[Cl:33][C:31]1[S:30][C:28]2[NH:29][C:25]([C:23]([NH:22][CH:14]3[CH2:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:12]([CH2:11][C:8]([N:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[O:9])[C:13]3=[O:34])=[O:24])=[CH:26][C:27]=2[CH:32]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 79341Piperidin-4-olHCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 100969462-Chloro-N-{1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 59%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Dimethylaminopyridine (5 mg, 0.038 mmol) and 4-hydroxypiperidine (42 mg, 0.41 mmol) were added to a suspension of N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 2; 150 mg, 0.38 mmol) and EDCI (79 mg, 0.41 mmol) in THF (0.5 mL) under an inert atmosphere. DMF (0.5 mL) was added and the mixture stirred at ambient temperature for 18 h. After pouring into water (10 mL) the resultant solid was filtered off and washed with 1M HCl aq. and water. Chromatography on silica gel (eluent gradient of CH2Cl2 to MeOH:CH2Cl2 (1:9)) afforded the title compound (109 mg, 59%) as an off white solid.

Workup

  1. filtrationwas filtered off
  2. washwashed with 1M HCl aq. and water

Sources & evidence

ORD record
ord-58b6a31d3a7e4952a59b5a823c0d804a
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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