Piperidine → HCID 52936531, compound

HRID 423232Notes

Reaction equation

HRID 423232 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[C:10]([O:23]C)=[N:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=3)[CH:14]=2)=[O:7])=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CN1C(=O)CCC1>[CH3:22][NH:21][C:17]1[N:16]=[C:15]([C:13]2[CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:25]=[CH:26][C:2]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:3][CH:4]=3)[C:10](=[O:23])[NH:11][CH:12]=2)[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 69368034HCID 69368034, compound

Product 1

HCID 52936531HCID 52936531, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

4-Bromo-N-(2-methoxy-5-(2-(methylamino)pyrimidin-4-yl)pyridin-3-yl)benzamide (50 mg, 0.121 mmol) was placed in a microwave tube equipped with a stirrer bar. NMP (1.5 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 (22 mg, 45% yield).). MS (ES+) m/e=405. 1H NMR (DMSO-d6) δH 1.54-1.61 (6H, m), 2.85 (3H, br s), 3.28-3.36 (4H, m), 6.95-7.12 (4H, m), 7.77 (2H, d), 8.00 (1H, s), 8.27 (1H, d), 9.02 (1H, br s), 9.09 (1H, s), 12.53 (1H, br s).

Workup

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

Sources & evidence

ORD record
ord-9224445efa694e2da356711940ae883e
Source dataset
uspto-grants-2012_01
Patent number
US08101770B2

Reaction notes

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