Methylamine → HCID 66989536, compound

HRID 2407783Notes

Reaction equation

HRID 2407783 reaction equation
[O:1]=[C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[C:31](Cl)(=[O:35])[C:32](Cl)=[O:33].[CH3:37][NH2:38]>C1(C)C=CC=CC=1>[CH3:37][NH:38][C:31](=[O:35])[C:32]([N:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:2](=[O:1])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:7][CH2:6]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:33]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 58504041HCID 58504041, compound

Product 1

HCID 66989536HCID 66989536, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound prepared in Example 303 (0.100 g) was suspended in toluene (10 mL) and oxalyl chloride (0.085 mL) added. The reaction mixture was stirred at room temperature for 2 hours. Methylamine solution (2 mol/L; 3.672 mL) was added and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was then partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material (0.173 g), which was used without further purification possessing the following physical data.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 1 hour
  2. customThe reaction mixture was then partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efaa85e0c69c4b23b3be98970479b557
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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