Triethylamine → Tert-butyl 4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)pyridin-2-yl)piperazine-1-carboxylate

HRID 557720Notes

Reaction equation

HRID 557720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]1([C:27]2[O:28][C:29]([C:35]([F:38])([F:37])[F:36])=[C:30]([C:32](O)=[O:33])[N:31]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:32]([C:30]3[N:31]=[C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:28][C:29]=3[C:35]([F:37])([F:38])[F:36])=[O:33])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733179PyBroPHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 52937267Tert-butyl 4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-(5-Amino-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester described above was mixed with 2-phenyl-5-trifluoromethyloxazole-4-carboxylic acid (771 mg, 3.0 mmol) and bromotrispyrrolidinophosphonium hexafluorophosphate (1.40 g, 3.0 mmol) in N,N-dimethylformamide (20 mL) and methylene chloride (5 mL) containing triethylamine (0.85 mL). The mixture was stirred at room temperature overnight and the solvents were evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent was evaporated. The residue was triturated with ethyl acetate and the solid was filtered to give 4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (1.09 g). LC-MS calcd for C25H26F3N5O4 (m/e) 517.5, obsd 518.1 (M+H). The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. customthe solvents were evaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate and solvent
  4. customwas evaporated
  5. customThe residue was triturated with ethyl acetate
  6. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-66475a16bc7e49eab281de4d84141a3f
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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