2-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide → HCID 10253024, compound

HRID 1247515Notes

Reaction equation

HRID 1247515 reaction equation
NC1CC2[C:5](=CC=CC=2)[N:4](CC2CO2)[C:3]1=O.[Cl:17][C:18]1[S:44][C:21]2[NH:22][C:23]([C:25]([NH:27][CH:28]3[CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([CH2:38][CH:39]([OH:42])[CH2:40]O)[C:29]3=[O:43])=[O:26])=[CH:24][C:20]=2[CH:19]=1>>[Cl:17][C:18]1[S:44][C:21]2[NH:22][C:23]([C:25]([NH:27][CH:28]3[CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([CH2:38][CH:39]([OH:42])[CH2:40][N:4]([CH3:5])[CH3:3])[C:29]3=[O:43])=[O:26])=[CH:24][C:20]=2[CH:19]=1

Participants

3

Reactant 2

HCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamideHCID 21906823HCID 21906823, compound

Product 1

HCID 10253024HCID 10253024, compound

Procedure

The title compound was prepared by a two-step coupling-epoxide opening sequence. Standard amide bond formation analogous to Method 3 except using 3-amino-1-(oxiran-2-ylmethyl)-3,4-dihydroquinolin-2(1H)-one (Method 19) as amine and 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (Method 9) as the acid component formed the title compound as a white solid which was used without further purification. The crude amide product (150 mg) was dissolved in EtOH (5 mL) followed by addition of dimethylamine in EtOH (5.0–6.0 M in EtOH, 0.5 mL) and the reaction was stirred overnight under argon. 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 2:9) afforded the title compound (41 mg) as a yellow solid.

Sources & evidence

ORD record
ord-ad68a029abb840848d87406dd75a968f
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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