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

HRID 23667
Notes
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Reaction equation

HRID 23667 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.[O:26]1[CH:30]=[CH:29][C:28]([CH:31]([OH:35])[CH2:32][NH:33][CH3:34])=[CH:27]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[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][N:33]([CH2:32][CH:31]([C:28]4[CH:29]=[CH:30][O:26][CH:27]=4)[OH:35])[CH3:34])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 102858031-(Furan-3-yl)-2-(methylamino)ethan-1-olHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 10152332N-(4-chlorobenzyl)-2-{[[2-(3-furyl)-2-hydroxyethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 81.6%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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), 1-(3-furyl)-2-(methylamino)ethanol (Preparation 64) (54 mg, 0.38 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5.0 mL) was stirred at room temperature for 24 hours. The solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile (5 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (102 mg) as a white solid.

Workup

  1. stirringThe resulting milky suspension was stirred vigorously for 30 minutes
  2. waitleft
  3. waitstanding overnight at room temp
  4. filtrationThe mixture was filtered
  5. washthe collected solid was washed with water
  6. customdried in vacuo
  7. customleaving a white solid
  8. customRecrystallization from acetonitrile (5 mL
  9. dissolutiondissolved
  10. temperaturewith warming
  11. temperaturecooled to 0° C. overnight)

Sources & evidence

ORD record
ord-709d6eb60e2b403cbb89de7a8b1c2ace
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852731B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes