4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 11200057, compound

HRID 917764Notes

Reaction equation

HRID 917764 reaction equation
[NH2:1][O:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH:17][C:18]1[C:19]([C:26](O)=[O:27])=[CH:20][N:21]([CH3:25])[C:22](=[O:24])[CH:23]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>O.CO>[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH:17][C:18]1[C:19]([C:26]([NH:1][O:2][CH2:3][CH2:4][OH:5])=[O:27])=[CH:20][N:21]([CH3:25])[C:22](=[O:24])[CH:23]=1

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 3014186Ethanol, 2-(aminooxy)-HCID 69508857HCID 69508857, compound

Product 1

HCID 11200057HCID 11200057, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

2-(Aminooxy)ethanol, 4-[(1-chloro-2-naphthyl)amino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid, DMT-MM and N-MM (2 eq) were reacted in 20% water/MeOH for 15 h according to the procedure outlined in example 33, step D. Further purification by flash chromatography on silica gel (EtOAc followed by 10% MeOH/CH2Cl2—100% MeOH gradient elution) gave 4-[(1-chloro-2-naphthyl)amino]-N-(2-hydroxyethoxy)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (24%). 1H NMR [400 MHz, (CD3)2SO] δ 11.72 (br s, 1H), 9.89 (br s, 1H), 8.20-8.14 (m, 1H), 7.98 (t, J=9.6 Hz, 2H), 7.74-7.67 (m, 2H), 7.61-7.56 (m, 2H), 5.69 (s, 1H), 4.78 (br s, 1H), 3.94 (t, J=4.8 Hz, 2H), 3.67-3.61 (m, 2H), 3.38 (s, 3H). LCMS (ACPI−) 386 (100%).

Workup

  1. customFurther purification by flash chromatography on silica gel (EtOAc followed by 10% MeOH/CH2Cl2—100% MeOH gradient elution)

Sources & evidence

ORD record
ord-52b1eeecffb148a3a62d7309073b1f98
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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