Dimethyl Sulfate → HCID 11427124, compound

HRID 917788Notes

Reaction equation

HRID 917788 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][C:13]=2[F:20])=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].S([O:28][CH3:29])(OC)(=O)=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][C:13]=2[F:20])=[CH:9][C:29](=[O:28])[N:7]([CH3:8])[CH:6]=1)=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 58962865HCID 58962865, compound

Product 1

HCID 11427124HCID 11427124, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Chloro-4-(4-ethyl-2-fluoro-phenylamino)-nicotinic acid ethyl ester (23.0 g, 72.0 mmol) was dissolved in CHCl3 (200 mL) and the solution cooled (ice/water). Dimethyl sulfate (42.0 mL, 432.0 mmol) was added, the solution allowed to warm to room temperature then heated at reflux for 20 hours as in Example 1, alternate Step B to give 4-(4-Ethyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester as a white solid (10.30 g, 45%). 1H NMR [(CDCl3, 400 MHz] δ 9.17 (s, 1H), 8.19 (s, 1H), 7.23 (dd, J=10.1, 1.9 Hz, 1H), 6.99 (dd, J=8.3, 1.0 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 5.76 (s, 1H), 4.33 (q, J=7.1 Hz, 2H), 3.52 (s, 3H), 2.64 (q, J=7.2 Hz, 2H), 1.39 (t, J=6.9 Hz, 3H), 1.23 (t, J=7.1 Hz, 3H). (APCI+) calcd for C17H19FN2O3 318.34 (M+1), found 319.1.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 20 hours as in Example 1, alternate Step B

Sources & evidence

ORD record
ord-8ef3dfaa48804d098c77643d68eb4226
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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