Methylamine → HCID 86646580, compound

HRID 2080551Notes

Reaction equation

HRID 2080551 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:11][S:12]C(=O)C)=[CH:4][CH:3]=1.CN>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:11][SH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86646579HCID 86646579, compound

Product 1

HCID 86646580HCID 86646580, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 1.23 gram (0.0041 mole) of 1-(2-{[(6-chloro(3-pyridyl))methyl](2-methylpropyl)amino}ethylthio)ethan-1-one (prepared in a manner analogous to Example 1, Step B) and 3.8 grams of a 33% solution of methylamine in ethanol (0.041 mole of methylamine) in 10 mL of ethanol was stirred at ambient temperature one hour. The reaction mixture was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, eluting with mixtures of ethyl acetate and hexanes. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.99 gram of 2-{[(6-chloro(3-pyridyl))-methyl](2-methylpropyl)amino}ethane-1-thiol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a residue
  2. customThe residue was purified by column chromatography on silica gel
  3. washeluting with mixtures of ethyl acetate and hexanes
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-66796b9da4a041b08bf9a95f4e2e4ce1
Source dataset
uspto-grants-2011_04
Patent number
US07932393B2

Reaction notes

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