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

HRID 23669Notes

Reaction equation

HRID 23669 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.Cl.Cl.[CH3:28][NH:29][CH2:30][CH:31]([C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1)[OH:32].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][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:29]([CH2:30][CH:31]([OH:32])[C:33]4[CH:34]=[CH:35][C:36]([N:39]5[CH2:40][CH2:41][O:42][CH2:43][CH2:44]5)=[CH:37][CH:38]=4)[CH3:28])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 225743592-(Methylamino)-1-(4-morpholin-4-ylphenyl)ethanol dihydrochlorideHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 10153225N-(4-chlorobenzyl)-2-{[[2-hydroxy-2-(4-morpholin-4-ylphenyl)ethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 51.1%

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), 2-(methylamino)-1-(4-morpholin-4-ylphenyl)ethanol dihydrochloride (Preparation 89) (118 mg, 0.38 mmol) and diisopropylethylamine (180 μL, 1.0 mmol) in dry DMF (5.0 mL) was stirred for 48 hours at room temperature. The solution was diluted with water (10 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 (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (76 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 (10 mL
  9. dissolutiondissolved
  10. temperaturewith warming
  11. temperaturecooled to 0° C. overnight)

Sources & evidence

ORD record
ord-ed6d8608a7274efa80fb323a24775399
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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