Piperidine → HCID 178517063, compound

HRID 2383568Notes

Reaction equation

HRID 2383568 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([CH:20]=O)=[CH:17][CH:18]=2)[CH:13]=[N:12]1.N1CCCCC1>CCO>[NH:11]1[C:19]2[C:14](=[CH:15][C:16](/[CH:20]=[C:3]3/[C:2](=[O:10])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:17][CH:18]=2)[CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 212506441H-Indazole-5-carboxaldehyde

Product 1

HCID 178517063HCID 178517063, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A scintillation vial was charged with indolin-2-one (67 mg, 0.500 mmol), 1H-indazole-5-carbaldehyde (73 mg, 0.550 mmol), piperidine (5.0 uL, 0.076 mmol) and EtOH (2 mL). The reaction was then heated to 90° C. for 2 hrs. The EtOH was removed and the product purified by preparatory reverse-phase HPLC to give 10 mg, 7.6% of the title compound. 1H NMR (400 MHz, CD3OD) δ 8.20-8.18 (m, 2H), 7.89 (s, 1H), 7.76 (d, J=7.9 Hz, 1H), 7.71-7.67 (m, 2H), 7.24 (t, J=7.4 Hz, 1H), 6.93 (d, J=7.7 Hz, 1H), 6.90 (t, J=7.5 Hz, 1H); MS ESI 262.0 [M+H]+, calcd for [C16H11N3O+H]+ 262.10.

Workup

  1. customThe EtOH was removed
  2. customthe product purified by preparatory reverse-phase HPLC

Sources & evidence

ORD record
ord-8c533dc821514c8ea48552a5317a2d32
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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