Methyl 2-fluoro-4-{5-[4-(2-methylpiperidin-1-yl)-3-nitrophenyl]-1,2,4-oxadiazol-3-yl}benzoate → Methyl 4-{5-[3-amino-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

HRID 219941Notes

Reaction equation

HRID 219941 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]4[CH3:29])=[C:19]([N+:30]([O-])=O)[CH:18]=3)[O:14][N:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CCO.C([O-])(O)=O.[Na+]>[NH2:30][C:19]1[CH:18]=[C:17]([C:15]2[O:14][N:13]=[C:12]([C:10]3[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=3)[N:16]=2)[CH:22]=[CH:21][C:20]=1[N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[CH3:29]

Participants

4

Reactant 1

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

Product 1

HCID 67528581Methyl 4-{5-[3-amino-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Stannous chloride dihydrate (20.49 g; 90.82 mmol) was added to a suspension of methyl 2-fluoro-4-{5-[4-(2-methylpiperidin-1-yl)-3-nitrophenyl]-1,2,4-oxadiazol-3-yl}benzoate, obtained in step 1, (8 g; 18.16 mmol) in EtOH (80 mL) and the resulting mixture was stirred at reflux for 3 hours. The solution was diluted with a saturated aqueous solution of NaHCO3 and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated affording the title compound as a yellow solid. 1H NMR (DMSO, 400 MHz) δ 8.18-7.95 (m, 3H), 7.56-7.55 (d, J=1.77 Hz, 1H), 7.44-7.41 (m, 1H), 7.21-7.19 (d, J=8.38 Hz, 1H), 5.32 (br s, 2H), 3.94 (s, 3H), 3.21-2.92 (m, 2H), 1.88-1.22 (m, 7H), 0.88 (d, J=6 Hz, 3H). LC/MS (Method B): 411.4 (M+H)+; 417.2 (M−H)−. HPLC: Rt 4.47 min (Purity: 95.6%).

Workup

  1. temperatureat reflux for 3 hours
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a3ae3c6d0dc543c9a0613bb40ec44cfb
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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