Potassium Carbonate → HCID 178418842, compound

HRID 2121472Notes

Reaction equation

HRID 2121472 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12](Cl)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH3:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[CH:1]1([C:4]2[CH:5]=[C:6]([NH:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([N:25]4[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]4)[N:11]=3)[NH:7][N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693814-MethylpiperidineHCID 21939162(2-Chloro-quinazolin-4-yl)-(5-cyclopropyl-2h-pyrazol-3-yl)-amine

Product 1

HCID 178418842HCID 178418842, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of (5-cyclopropyl-1H-pyrazol-3-yl)-(2-chloro-quinazolin-4-yl)-amine (118 mg, 0.41 mmol) in tert-butanol (3.0 mL) was added 4-methylpiperidine (0.49 mL, 4.1 mmol) and the reaction mixture heated at reflux overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in a mixture EtOH:water (1:3, 4 mL). Potassium carbonate (57 mg, 0.41 mmol) was added and the mixture stirred at room temperature for 2 hours. The resulting suspension was filtered, washed with water (×2), and rinsed with Et2O (×2) to afford III-111 as a white solid (123 mg, 85%): mp 190° C.; 1H NMR (DMSO) δ 0.66 (2H, s), 0.93 (5H, br s), 1.07 (2H, d), 1.66 (3H, s), 1.91 (1H, s), 2.85 (2H, t), 4.72 (2H, d), 6.33 (1H, s), 7.06 (1H, t), 7.29 (1H, d), 7.52 (1H, t), 8.31 (1H, d), 9.95 (1H, s), 12.18 (1H, br s); IR (solid) 2925, 2852, 1622, 1590, 1581, 1558, 1494, 1481, 1453, 1435, 1394; MS 349.2 (M+H)+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in a mixture EtOH:water (1:3, 4 mL)
  5. filtrationThe resulting suspension was filtered
  6. washwashed with water (×2)
  7. washrinsed with Et2O (×2)

Sources & evidence

ORD record
ord-3fb18c388c2f45f888efb2f5c2466d74
Source dataset
uspto-grants-2004_02
Patent number
US06696452B2

Reaction notes

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