Acetic Acid → HCID 66818342, compound

HRID 1755095Notes

Reaction equation

HRID 1755095 reaction equation
C(O)(=O)C.[C:5]([O:9][C:10]([N:12]1[CH2:24][CH2:23][C:15]2([N:19]=[C:18](SC)[NH:17][C:16]2=[O:22])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].C(=O)(O)[O-].[Na+]>CC(N(C)C)=O>[C:5]([O:9][C:10]([N:12]1[CH2:24][CH2:23][C:15]2([N:19]=[C:18]([NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[C:27]([C:26]([F:25])([F:34])[F:35])[CH:28]=3)[NH:17][C:16]2=[O:22])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 516892Sodium BicarbonateHCID 66818075HCID 66818075, compound

Product 1

HCID 66818342HCID 66818342, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Acetic acid (0.275 ml, 4.8 mmol) was added to a solution of 2-methylsulfanyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (72 mg, 0.24 mmol) and m-trifluoromethylaniline (0.150 ml, 1.2 mmol) in DMA (1.0 ml), and the mixture was irradiated with microwaves at 150° C. for 20 minutes. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layers were combined, washed with saturated brine and dried over magnesium sulfate, and the solvent was then distilled off. The residue was purified by silica gel column chromatography to give 4-oxo-2-(3-trifluoromethyl-phenylamino)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (50 mg, 51%).

Workup

  1. customthe mixture was irradiated with microwaves at 150° C. for 20 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was then distilled off
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0cdb3275250c4181a0cd65f0c2c3e84d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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