Methylamine → HCID 71150687, compound

HRID 407254Notes

Reaction equation

HRID 407254 reaction equation
ClC1=[C:3]([C:21]([O:23][CH3:24])=[O:22])[NH:4][CH:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:6]/[C:7]/1=[N:8]\OS(C)(=O)=O.[CH3:25][NH2:26].[CH2:27]1COCC1>CS(C)=O.O>[NH2:26][C:25]1[C:3]([C:21]([O:23][CH3:24])=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:6][C:7]=1[NH:8][CH3:27]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 178498359HCID 178498359, compound

Product 1

HCID 71150687HCID 71150687, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution (E)-methyl 3-chloro-6-(4-chlorophenyl)-4-(((methylsulfonyl)oxy)imino)-1,4,5,6-tetrahydropyridine-2-carboxylate (100 mg, 0.254 mmol) in DMSO (2 mL) was added 2 M methanamine in THF (0.8 mL, 1.6 mmol). The reaction mixture was stirred at ambient temp for 30 min, and then it was diluted with H2O. The product crashed out of solution, and was collect in a Buchner funnel, and dried under vacuum to yielded a brown solid (49 mg, 66%): mp 178-200° C.; 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.5 Hz, 1H), 6.95 (s, 1H), 5.39 (s, 1H), 4.07 (s, 1H), 3.98 (s, 1H), 2.98 (d, J=5.1 Hz, 1H); ESIMS m/z 292 ([M+H]+), 290 ([M−H]−).

Workup

  1. customwas collect in a Buchner funnel
  2. customdried under vacuum

Sources & evidence

ORD record
ord-48192119363c4402b825da444191a501
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

Loading…