Methylamine → HCID 18324829, compound

HRID 1250893Notes

Reaction equation

HRID 1250893 reaction equation
CN.[CH2:3]([N:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])C1=S)C=C>C(O)C.ClCCl>[Cl:18][C:17]1[C:12]([NH:8][CH2:9][CH2:10][CH2:11][NH:6][CH3:3])=[C:13]([CH3:19])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 9925711HCID 9925711, compound

Product 1

HCID 18324829HCID 18324829, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To an 8.03 M solution of methylamine in ethanol (31 mL) was added the hydrobromide salt of Example 12, Step B (8.6 g) and the mixture was stirred at ambient temperature for 17 hours. The ethanol was removed in vacuo and the residue was partitioned between dichloromethane and 1N sodium hydroxide. The organic phase was washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a yellow oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 98:2 to 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide) gave the title compound (3.9 g, 84.1%) as a pale yellow oil, which was used as such in the next step.

Workup

  1. customThe ethanol was removed in vacuo
  2. customthe residue was partitioned between dichloromethane and 1N sodium hydroxide
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with a solvent gradient (from 98:2 to 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide)

Sources & evidence

ORD record
ord-01f36d65cf3f4a5dae426ae9df342219
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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