Water → N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-(3-methoxyphenyl)-ethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide

HRID 1814872Notes

Reaction equation

HRID 1814872 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]([OH:22])[CH2:19][NH:20][CH3:21])[CH:15]=[CH:16][CH:17]=1.[Cl:23][C:24]1[CH:46]=[CH:45][C:27]([CH2:28][NH:29][C:30]([C:32]2[C:33](=[O:44])[C:34]3[CH:41]=[C:40]([CH2:42]Cl)[O:39][C:35]=3[N:36]([CH3:38])[CH:37]=2)=[O:31])=[CH:26][CH:25]=1.O>CN(C=O)C>[Cl:23][C:24]1[CH:46]=[CH:45][C:27]([CH2:28][NH:29][C:30]([C:32]2[C:33](=[O:44])[C:34]3[CH:41]=[C:40]([CH2:42][N:20]([CH2:19][CH:18]([OH:22])[C:14]4[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH3:10])[CH:13]=4)[CH3:21])[O:39][C:35]=3[N:36]([CH3:38])[CH:37]=2)=[O:31])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 134873MethylphenylephrineHCID 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10174566N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-(3-methoxyphenyl)-ethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Diisopropylethylamine (0.11 mL) and 1-(3-methoxyphenyl)-2-(methylamino)ethanol (Preparation 31, 0.112 g) were added to a suspension of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 2, 0.150 g) in DMF (10 mL). The reaction mixture was heated to 90° C. for 1 h. The mixture was allowed to cool to room temperature and was poured into water (25 mL). The suspension was filtered and the resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.102 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 116-120° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 7.41-7.32, 7.18, 6.88-6.85, 6.77-6.75, 5.10, 4.704.66, 4.55, 3.89, 3.74, 3.70, 2.61, 2.33; MS (ESI+) m/z 510 (M+H)+. Anal. Found: C, 63.48; H, 5.56; N, 8.24; Cl, 6.94.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe suspension was filtered
  3. customthe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2)
  4. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b00433bb467a4ca780de32404ad351b9
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

Loading…