N-Methylphenylethanolamine → N-(4-chlorobenzyl)-2-(((2-hydroxy-2-phenylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 1978962

Reaction equation

HRID 1978962 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[CH:19]=[C:18]([CH2:20]O)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS(Cl)(=O)=O.[CH3:39][NH:40][CH2:41][CH:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[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[CH:19]=[C:18]([CH2:20][N:40]([CH2:41][CH:42]([OH:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH3:39])[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 913N-MethylphenylethanolamineHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 6482399N-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-7-methyl-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10458488N-(4-chlorobenzyl)-2-(((2-hydroxy-2-phenylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamideYield 63.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (0.300 g) from Example No. 35 in DMF (17 mL) are added DMAP (16 mg), 2,4,6-collidine (0.27 mL), and methanesulfonyl chloride (0.16 mL). The reaction mixture is stirred at room temperature for 1 h and then α-(methylaminomethyl)benzyl alcohol (1.26 g) is added. The mixture is stirred at room temperature for 18 h and is then poured into water (50 mL). The resulting off-white solid is filtered off and purified by column chromatography (CH2Cl2/methanol, 99/1; 97/3) to yield 0.261 g (63%) of the title compound as a pale yellow solid.

Workup

  1. stirringThe mixture is stirred at room temperature for 18 h
  2. filtrationThe resulting off-white solid is filtered off
  3. custompurified by column chromatography (CH2Cl2/methanol, 99/1; 97/3)

Sources & evidence

ORD record
ord-9b7cc8f6848444c88a1ae3b3c78c4462
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Linked notes

Loading…