Diisopropylethylamine → 2-{[{2-[3-(acetylamino)phenyl]-2-hydroxyethyl}(methyl)amino]methyl}-N-(4-chlorobenzyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23663Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[OH:26][CH:27]([C:31]1[CH:32]=[C:33]([NH:37][C:38](=[O:40])[CH3:39])[CH:34]=[CH:35][CH:36]=1)[CH2:28][NH:29][CH3:30].C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:38]([NH:37][C:33]1[CH:32]=[C:31]([CH:27]([OH:26])[CH2:28][N:29]([CH2:20][C:18]2[S:19][C:12]3[C:11](=[O:23])[C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=4)=[O:9])=[CH:15][N:14]([CH3:16])[C:13]=3[C:17]=2[CH3:22])[CH3:30])[CH:36]=[CH:35][CH:34]=1)(=[O:40])[CH3:39]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.25 mmol), N-{3-[1-hydroxy-2-(methylamino)ethyl]phenyl}acetamide (Preparation 45) (79 mg, 0.38 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 6 hours at that temperature. After cooling to room temperature, the solution was concentrated under high vacuum. The oil residue was purified with a silica gel chromatotron plate to give the title compound (62 mg) as a white solid.

Workup

temperatureAfter cooling to room temperature
concentrationthe solution was concentrated under high vacuum
customThe oil residue was purified with a silica gel chromatotron plate

Sources & evidence

ORD record: ord-3ab98c0e9d844186809171759ad33079
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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