Dimethyl Sulfoxide → HCID 71150652, compound

HRID 407253Notes

Reaction equation

HRID 407253 reaction equation
Cl[C:2]1=[C:3]([C:24]([O:26][CH3:27])=[O:25])[NH:4][CH:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[CH2:6]/[C:7]/1=[N:8]\OS(C)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:34][S-].[Na+].[CH3:37][S:38](C)=O>>[NH2:8][C:7]1[CH:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:4]=[C:3]([C:24]([O:26][CH2:27][CH3:34])=[O:25])[C:2]=1[S:38][CH3:37]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 4378561Sodium methanethiolateHCID 178498360HCID 178498360, compound

Product 1

HCID 71150652HCID 71150652, compoundYield 34%

Procedure

To a solution of (E)-methyl 3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-(((methylsulfonyl)oxy)imino)-1,4,5,6-tetrahydropyridine-2-carboxylate (200 mg, 0.44 mmol) in DMSO (1.4 mL) was added K2CO3 (181 mg, 1.3 mmol) followed by sodium thiomethoxide (93 mg, 1.3 mmol). After 10 min the reaction was quenched with 1 M HCl solution and then extracted with diethyl ether. The organics were washed with brine, dried with Na2SO4, filtered and purified by silica gel chromatography eluting with 30% Et2O in pentane to yielded to afford a brown solid (56 mg, 34%): mp 93-94° C.; 1H NMR (300 MHz, CDCl3) δ 7.67 (dd, J=8.6, 7.7 Hz, 1H), 7.22 (m, 1H), 7.11 (d, J=1.9 Hz, 1H), 5.16 (s, 2H), 4.47 (q, J=7.1 Hz, 2H), 3.96 (d, J=0.9 Hz, 3H), 2.30 (d, J=1.7 Hz, 3H), 1.43 (t, J=7.1 Hz, 3H); ESIMS m/z 369 ([M−H]−).

Workup

  1. customAfter 10 min the reaction was quenched with 1 M HCl solution
  2. extractionextracted with diethyl ether
  3. washThe organics were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. custompurified by silica gel chromatography
  7. washeluting with 30% Et2O in pentane
  8. customto yielded

Sources & evidence

ORD record
ord-8861005b40ce4d5cb846c8967222ad8e
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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