Methylamine → HCID 11750948, compound

HRID 1640402Notes

Reaction equation

HRID 1640402 reaction equation
[CH3:1][NH2:2].[F:3][C:4]([F:34])([F:33])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]([O:30]CC)=O)=[O:25])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>O1CCCC1.CO>[F:3][C:4]([F:33])([F:34])[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][N:21]([C:24]([O:26][CH2:27][C:28]([NH:2][CH3:1])=[O:30])=[O:25])[CH2:22][CH2:23]3)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 60209547HCID 60209547, compound

Product 1

HCID 11750948HCID 11750948, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.10 ml (14.15 mmol) of a solution of methylamine (2M) in tetrahydrofuran are added to a solution of 1.60 g (3.54 mmol) of 2-(ethyloxy)-2-oxoethyl 4-{4′-[(trifluoromethyl)oxy]-4-biphenylyl}-1-piperazinecarboxylate, prepared in step 1.3, in 14 ml of methanol. Stirring is continued at room temperature for 12 hours. After concentrating under reduced pressure, the residue obtained is purified by chromatography on silica gel, eluting with a 97/3 mixture of dichloromethane and methanol. A solid is obtained, and is recrystallized from a mixture of ethyl acetate and diisopropyl ether. 0.86 g of pure product is thus obtained in the form of a white solid.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue obtained
  3. customis purified by chromatography on silica gel
  4. washeluting with a 97/3 mixture of dichloromethane and methanol
  5. customA solid is obtained
  6. customis recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-1d75557b214248508fdc0856d7460792
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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