4-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acid → Methyl 2-fluoro-4-{5-[4-(2-methylpiperidin-1-yl)-3-nitrophenyl]-1,2,4-oxadiazol-3-yl}benzoate

HRID 219940Notes

Reaction equation

HRID 219940 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].[NH2:20][C:21](=[N:33]O)[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([F:32])[CH:23]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[F:32][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:12]([C:11]3[CH:15]=[CH:16][C:8]([N:3]4[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]4[CH3:1])=[C:9]([N+:17]([O-:19])=[O:18])[CH:10]=3)[O:14][N:33]=2)[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 2

HCID 431767024-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acidHCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 67528992Methyl 2-fluoro-4-{5-[4-(2-methylpiperidin-1-yl)-3-nitrophenyl]-1,2,4-oxadiazol-3-yl}benzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Intermediate 11 (12.46 g; 47.13 mmol) was dissolved in DCM (200 mL) and n,n′-dicyclohexylcarbodiimide (11.67 g; 56.56 mmol) was added. Then Intermediate 1 was added (10 g; 47.13 mmol) and the suspension was stirred at RT for 12 hours. The precipitate was filtered off and the solvent evaporated to give a yellow solid. The residue was dissolved in Toluene (300 mL) and Py (150 mL) and the solution was heated to 130° C. for 12 hours. The reaction mixture was concentrated to afford a yellow sticky oil which was precipitated from ACN affording the title compound as a yellow solid. LC/MS (Method B): 441.3 (M+H)+ HPLC: Rt 5.86 min (Purity: 95.1%).

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe solvent evaporated
  3. customto give a yellow solid
  4. temperaturePy (150 mL) and the solution was heated to 130° C. for 12 hours
  5. concentrationThe reaction mixture was concentrated
  6. customto afford a yellow sticky oil which
  7. customwas precipitated from ACN affording the title compound as a yellow solid

Sources & evidence

ORD record
ord-0df5dd627ccf4d15b4245c25d38afc26
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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