4-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidin-1-yl)-benzoic acid tert-butyl ester → HCID 46833515, compound

HRID 1510294Notes

Reaction equation

HRID 1510294 reaction equation
C([O:5][C:6](=[O:43])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]4[N:29]=[C:30]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[O:31][C:32]=4[C:33]([F:36])([F:35])[F:34])=[O:27])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[C:37]1([C:30]2[O:31][C:32]([C:33]([F:34])([F:35])[F:36])=[C:28]([C:26]([NH:25][C:22]3[CH:21]=[CH:20][C:19]([CH:16]4[CH2:15][CH2:14][N:13]([C:10]5[CH:9]=[CH:8][C:7]([C:6]([OH:43])=[O:5])=[CH:12][CH:11]=5)[CH2:18][CH2:17]4)=[CH:24][CH:23]=3)=[O:27])[N:29]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 1

HCID 674271094-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidin-1-yl)-benzoic acid tert-butyl ester

Product 1

HCID 46833515HCID 46833515, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The above 4-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidin-1-yl)-benzoic acid tert-butyl ester (40 mg) was dissolved in a mixture of methylene chloride (2 mL) and trifluoroacetic acid (2 mL). The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was extracted with ethyl acetate and water. The organic layer was dried and solvents were evaporated. The residue was triturated with ethyl acetate to give a solid as 4-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidin-1-yl)-benzoic acid (25 mg). LC-MS for C29H24F3N3O4 (m/e) calcd 535, obsd 536 (M+H). 1H-NMR is consistent with the desired structure.

Workup

  1. customsolvents were evaporated
  2. extractionThe residue was extracted with ethyl acetate and water
  3. customThe organic layer was dried
  4. customsolvents were evaporated
  5. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-5fb5cd5923a84ec28dd8b7c17af26d2b
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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