Potassium Carbonate → HCID 178418842, compound

HRID 397355Notes

Reaction equation

HRID 397355 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) δ0.66 (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-5e0e62a631554b07b1f58b51b31e2601
Source dataset
uspto-grants-2003_08
Patent number
US06610677B2

Reaction notes

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