Imidazole → 6-(2-((1H-imidazol-1-yl)(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

HRID 1028951Notes

Reaction equation

HRID 1028951 reaction equation
Cl.Cl[CH:3]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([NH2:21])[C:15]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[CH:14]2.[NH:34]1[CH:38]=[CH:37][N:36]=[CH:35]1>C(#N)C>[N:34]1([CH:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=2[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[C:16]([NH2:21])[C:15]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:14]3)[CH:38]=[CH:37][N:36]=[CH:35]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 673478476-(2-(Chloro(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine hydrochloride

Product 1

HCID 673468076-(2-((1H-imidazol-1-yl)(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a small, sealed Smith synthesizer vial, 6-(2-(chloro(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine hydrochloride (0.030 g, 0.062 mmol) and imidazole (0.021 g, 0.312 mmol) were treated with ACN (0.416 mL). The solution was stirred at ambient temperature for 1 h. The reaction mixture was warmed to 100° C. for 1 h and then allowed to cool to ambient temperature. The mixture was purified by HPLC (1-70% acetonitrile/H2O, TFA modifier). A single clean fraction was treated with NH4OH and concentrated to ¼ volume. The resulting precipitate was collected and dried under a stream of N2 to afford 6-(2-((1H-imidazol-1-yl)(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine. MS (ESI, pos. ion) m/z: 476 (M+1).

Workup

  1. customIn a small, sealed Smith synthesizer vial
  2. temperatureThe reaction mixture was warmed to 100° C. for 1 h
  3. temperatureto cool to ambient temperature
  4. customThe mixture was purified by HPLC (1-70% acetonitrile/H2O, TFA modifier)
  5. additionA single clean fraction was treated with NH4OH
  6. concentrationconcentrated
  7. customThe resulting precipitate was collected
  8. dry with materialdried under a stream of N2

Sources & evidence

ORD record
ord-c8a370cbcf334242a34a94428d4fbea8
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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