HCID 66738506, compound → HCID 52937158, compound

HRID 1691883Notes

Reaction equation

HRID 1691883 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:24]=[C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:26][C:27]=3[C:28]([F:31])([F:30])[F:29])=[O:22])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[N:15]1[CH:16]=[C:17]([NH:20][C:21]([C:23]2[N:24]=[C:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:26][C:27]=2[C:28]([F:30])([F:31])[F:29])=[O:22])[CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 66738506HCID 66738506, compound

Product 1

HCID 52937158HCID 52937158, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (535 mg) from above was dissolved in a mixture of methylene chloride (35 mL) and trifluoroacetic acid (9 mL). The mixture was stirred at room temperature for 2 hrs. The solvents were evaporated and the residues were partitioned between methylene chloride and dilute sodium hydroxide solution. The organic layer was washed with brine and dried over sodium sulfate. Evaporation of solvents gave 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl-5-yl)-amide (360 mg) as a solid. LC-MS calcd for C21H19F3N4O2 (m/e) 416.1, obsd 417.1 (M+H). The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. customThe solvents were evaporated
  2. customthe residues were partitioned between methylene chloride and dilute sodium hydroxide solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvents

Sources & evidence

ORD record
ord-ce5c5ada26de4f54a26757aa97fd993e
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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