Methylamine → HCID 15053465, compound

HRID 974561Notes

Reaction equation

HRID 974561 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13][NH2:14].[C:15](O)(=O)[C:16](O)=O.[F:21][C:22]([F:35])([F:34])[C:23]1[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=1)[O:26]C1CNC1.[CH2:36](N(CC)CC)C>C(Cl)Cl>[CH3:36][C:15](=[CH2:16])[CH2:13][NH:14][C:1]([N:8]1[CH2:9][CH:11]([O:26][C:25]2[CH:31]=[CH:32][CH:33]=[C:23]([C:22]([F:21])([F:34])[F:35])[CH:24]=2)[CH2:12]1)=[O:2]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19799580HCID 19799580, compound

Product 1

HCID 15053465HCID 15053465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole in 75 ml of methylene chloride was stirred under nitrogen while 1.6 g (0.022 mole) of methylamine was added with a syringe and needle through a septum installed in one neck of the reaction flask. The reaction was slightly exothermic. The reaction mixture was stirred for 1 hr, then treated with 6.2 g (0.02 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate followed in 0.5 hr with 5 ml of triethylamine and stirring continued for 16 hr. The reaction mixture was washed with 2×30 ml of water, dried over magnesium sulfate, and concentrated on a rotary evaporator to yield 6.7 g of oily residue which solidified. The residue was recrystallized from isopropyl ether to yield 5.4 g (85.9%) of fine white crystals, m.p. 90°-91° C.

Workup

  1. additionwas added with a syringe
  2. stirringstirring
  3. waitcontinued for 16 hr
  4. washThe reaction mixture was washed with 2×30 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-c7e74572a99f4be9b953abe6475a8cc2
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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