Benzylamine → HCID 58659442, compound

HRID 1993516Notes

Reaction equation

HRID 1993516 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)(C)C>[CH2:29]([NH:36][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:21][CH:20]=3)=[O:17])=[CH:13][CH:14]=2)[N:5]=[CH:4][N:3]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 58659380HCID 58659380, compound

Product 1

HCID 58659442HCID 58659442, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Under N2-atmosphere, a suspension of N-(4-(4-chloropyrimidin-6-yl-oxy)-phenyl)-N′-(4-tert-butylphenyl)-urea (397 mg, 1.00 mmol) and benzylamine (327 μM) in isopropanol (3 ml) is stirred for 21 h at 70° C. Then the reaction mixture is concentrated in vacuo, the residue re-dissolved in saturated NaHCO3 solution and AcOEt, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. The crude product is dissolved in CH2Cl2 and after addition of SiO2 again concentrated. The resulting powder is put on top of a SiO2-column and eluted with AcOEt/hexane 3:1, yielding the title compound: m.p.: 118-120° C.; 1H-NMR (DMSO-d6): 8.73 (s, HN), 8.62 (s, HN), 8.13 (s, 1H), 7.84 (s, HN), 7.46 (d, 2H), 7.35 (d, 2H), 7.30 (m, 4H), 7.28 (m, 2H), 7.24 (m, 1H), 7.03 (d, 2H), 5.78 (s, 1H), 4.49 (s, 2H), 1.26 (Me3C).

Workup

  1. concentrationThen the reaction mixture is concentrated in vacuo
  2. dissolutionthe residue re-dissolved in saturated NaHCO3 solution
  3. customAcOEt, the aqueous layer separated off
  4. extractionextracted twice with AcOEt
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. dissolutionThe crude product is dissolved in CH2Cl2
  9. additionafter addition of SiO2
  10. concentrationagain concentrated
  11. washeluted with AcOEt/hexane 3:1

Sources & evidence

ORD record
ord-62ae371faba24d6ab8e0818841cf38a4
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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