Piperidine → HCID 52936434, compound

HRID 423227Notes

Reaction equation

HRID 423227 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[C:10](=[O:21])[NH:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH:14]=2)=[O:7])=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN1C(=O)CCC1>[O:21]=[C:10]1[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:3][CH:4]=2)=[CH:14][C:13]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:12][NH:11]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 11639271HCID 11639271, compound

Product 1

HCID 52936434HCID 52936434, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

4-Bromo-N-(1,2-dihydro-2-oxo-5-(pyridin-4-yl)pyridin-3-yl)benzamide (30 mg, 0.081 mmol) I-20 was placed in a microwave tube equipped with a stirrer bar. NMP (0.75 mL) was added, followed by piperidine (1.5 mL). The reaction vessel was heated at 160° C. for 2 hours in a microwave. After cooling, the solvent and excess piperidine were removed in vacuo. The crude compound was recrystallized from methanol to give the title compound as a white solid (13 mg, 43% yield).). MS (ES+) m/e=375. 1H NMR (DMSO-d6) δH 1.54-1.65 (6H, m), 3.30-3.38 (4H, m), 7.02 (2H, d), 7.61 (2H, d) 7.72-7.80 (1H, m), 7.78 (2H, d), 8.59 (2H, d), 8.77 (1H, d), 9.13 (1H, s), 12.58 (1H, bs).

Workup

  1. customwas placed in a microwave tube
  2. customequipped with a stirrer bar
  3. temperatureAfter cooling
  4. customthe solvent and excess piperidine were removed in vacuo
  5. customThe crude compound was recrystallized from methanol

Sources & evidence

ORD record
ord-6f8d6fac86ed4812b5138cca33e3f0dc
Source dataset
uspto-grants-2012_01
Patent number
US08101770B2

Reaction notes

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