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

HRID 982725Notes

Reaction equation

HRID 982725 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20]Cl)=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]([OH:36])[CH2:33][NH:34][CH3:35])[CH:29]=[CH:30][CH:31]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]([OH:36])[CH2:33][N:34]([CH2:20][C:18]2[S:19][C:12]3[C:11](=[O:22])[C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=4)=[O:9])=[CH:15][N:14]([CH3:16])[C:13]=3[CH:17]=2)[CH3:35])[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 30276171-(m-Aminophenyl)-2-methylaminoethanolHCID 22563229N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 103114422-{[[2-(3-aminophenyl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (80 mg, 0.21 mmol), 1-(3-aminophenyl)-2-(methylamino)ethanol (Zhur. Obshchei Khim. (J. Gen. Chem.) 1952, 22, 496-502)(53 mg, 0.32 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 5 hours at that temperature. After cooling to room temperature, the solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight in the refrigerator. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile/water (dissolved with warming 5 mL of acetonitrile, then cooled to 0° C. and then diluted with 3 mL of water, left overnight) gave the title compound (62 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-b9eb8290d7d74cc8a522f53be368d4bd
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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