Pyridine → HCID 178501868, compound

HRID 2367132Notes

Reaction equation

HRID 2367132 reaction equation
S(O)(O)(=O)=[O:2].[CH3:6][S:7][C:8](=[NH:10])[NH2:9].N1C=CC=CC=1.Cl[C:18](=[O:23])[C:19]([O:21][CH3:22])=[O:20].[C:24]([O:27][CH2:28]C)(=[O:26])[CH3:25]>ClCCl>[CH3:22][O:21][C:19](=[O:20])[C:18](/[N:10]=[C:8](/[NH:9][C:25](=[O:2])[C:24]([O:27][CH3:28])=[O:26])\[S:7][CH3:6])=[O:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 752702-Methyl-2-thiopseudourea sulfateHCID 79846Methyl chloroglyoxylate

Product 1

HCID 178501868HCID 178501868, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-methyl-2-thiopseudourea sulfate (1.50 g, 10.80 mmol) in dichloromethane (50 mL) and pyridine (1.76 mL, 21.60 mmol) at 0° C. a solution of methyl chlorooxoacetate (1.0 mL, 10.80 mmol) in dichloromethane (10.0 mL) was added and the reaction mixture was stirred for 15 hours at room temperature. Ethyl acetate (150 mL) was added into the mixture and it was washed with 1M aqueous hydrochloric acid and brine. The solvent was dried over anhydrous sodium sulfate. Filtration and concentration, followed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:3 to 3:2 eluent) gave methyl{[(1Z)-{[(methyloxy)(oxo)acetyl]amino}(methylthio)methylidene]amino}(oxo)acetate (0.87 g, 31% yield). 1H NMR (400 MHz, DMSO-d6): 12.48 (br.s, 2H), 3.81 (s, 3H), 2.41 (s, 3H); MS (EI) for C8H10N2O6S: 263 (MH+).

Workup

  1. additionwas added
  2. washwas washed with 1M aqueous hydrochloric acid and brine
  3. dry with materialThe solvent was dried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration
  5. customfollowed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:3 to 3:2 eluent)

Sources & evidence

ORD record
ord-f4ee8b8ab3c747bc9fdf26445fe5836e
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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