Triethylamine → tert-butyl (4-(4-((1-methyl-3-(2-oxo-1,3-oxazolidin-3-yl)-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamate

HRID 632805Notes

Reaction equation

HRID 632805 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-])=O)[C:4]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])=[N:3]1.[C:16]([O:20][C:21]([N:23]([CH2:49][C:50]([F:53])([F:52])[F:51])[C:24]1[CH:29]=[C:28]([C:30]2[O:31][CH:32]=[C:33]([C:35](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:36])[N:34]=2)[CH:27]=[CH:26][N:25]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>CO.[C].[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:35]([C:33]2[N:34]=[C:30]([C:28]3[CH:27]=[CH:26][N:25]=[C:24]([N:23]([CH2:49][C:50]([F:52])([F:51])[F:53])[C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:29]=3)[O:31][CH:32]=2)=[O:36])[C:4]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])=[N:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1180610553-(1-Methyl-4-nitro-1h-pyrazol-3-yl)-2-oxazolidinoneHCID 118061096Pentafluorophenyl 2-(2-((tert-butoxycarbonyl) (2,2,2-trifluoroethyl)amino)pyridin-4-yl)-1,3-oxazole-4-carboxylate

Product 1

HCID 131735461tert-butyl (4-(4-((1-methyl-3-(2-oxo-1,3-oxazolidin-3-yl)-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamateYield 18.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(1-methyl-4-nitro-1H-pyrazol-3-yl)-1,3-oxazolidin-2-one (58 mg), pentafluorophenyl 2-(2-((tert-butoxycarbonyl) (2,2,2-trifluoroethyl)amino)pyridin-4-yl)-1,3-oxazole-4-carboxylate (197 mg), 10% palladium-carbon (29 mg) and triethylamine (76 μL) in methanol (1.4 mL) was stirred overnight at room temperature under hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (28 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c0bb9377477540fd82fef65b756c8f74
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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