4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 11325138, compound

HRID 917745Notes

Reaction equation

HRID 917745 reaction equation
[NH2:1][O:2][CH2:3][CH2:4][OH:5].[F:6][C:7]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:8]=1[NH:9][C:10]1[C:11]([C:18](O)=[O:19])=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CO>[F:6][C:7]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:8]=1[NH:9][C:10]1[C:11]([C:18]([NH:1][O:2][CH2:3][CH2:4][OH:5])=[O:19])=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=1

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 3014186Ethanol, 2-(aminooxy)-HCID 23630798HCID 23630798, compound

Product 1

HCID 11325138HCID 11325138, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Aminooxy)ethanol, 4-(2-fluoro-4-methylanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and DMT-MM were reacted in MeOH as outlined in example 33, step D. Further purification by flash chromatography on silica gel (EtOAc followed by 10% MeOH/CH2Cl2) gave 4-(2-fluoro-4-methylanilino)-N-(2-hydroxyethoxy)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (61%) as a cream solid; m.p. (EtOAc/Hexane) 110-115° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.62 (br s, 1H), 9.21 (br s, 1H), 8.11 (s, 1H), 7.31 (t, J=8.3 Hz, 1H), 7.17 (d, J=11.8 Hz, 1H), 7.06 (d, J=8.3 Hz, 1H), 5.38 (s, 1H), 4.75 (t, J=5.3 Hz, 1H), 3.91 (t, J=4.9 Hz, 2H), 3.62 (q, J=4.9 Hz, 2H), 3.35 (s, 3 H, obscured), 2.32 (s, 3H). LCMS (ACPI−) 334 (50%). Anal. Calcd for C16H18FN3O4.0.25 H2O: C, 56.6; H, 5.5; N, 12.4. Found C, 56.5; H, 5.5; N, 12.1.

Workup

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

Sources & evidence

ORD record
ord-0145dca1b934446fa30d3ff941e5d70a
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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