Water → HCID 21082055, compound

HRID 347016Notes

Reaction equation

HRID 347016 reaction equation
[NH3:1].CC(O)C.Cl[C:7]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH3:32])[C:27](=[O:33])[CH:26]=[C:25]2[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)([C:16]1[N:20]([CH3:21])[CH:19]=[N:18][CH:17]=1)[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.O>C1COCC1>[NH2:1][C:7]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH3:32])[C:27](=[O:33])[CH:26]=[C:25]2[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)([C:16]1[N:20]([CH3:21])[CH:19]=[N:18][CH:17]=1)[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 21082056HCID 21082056, compound

Product 1

HCID 21082055HCID 21082055, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NH3/iPrOH (6 ml) was added dropwise at 5° C. to a solution of 4-[chloro[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl](1-methyl-1H-imidazol-5-yl)methyl]-benzonitrile (0.00121 mol), (obtained in stage c), in THF (7 ml). The mixture was stirred at room temperature for 4 hours, poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: toluene/iPrOH/NH4OH; 90/10/1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.3 g (52%) which were then purified by column chromatography over kromasil (eluent: CH3CN/NH4OAc; 40/60; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.18 g (31%) which were crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 0.13 g (22%) of 4-[amino[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6quinolinyl](1-methyl-1H-imidazol-5-yl)methyl]-benzonitrile, melting point 245° C.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: toluene/iPrOH/NH4OH; 90/10/1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customyielding 0.3 g (52%) which
  10. customwere then purified by column chromatography over kromasil (eluent: CH3CN/NH4OAc; 40/60; 15–40 μm)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated
  13. customyielding 0.18 g (31%) which
  14. customwere crystallized from CH3CN/diethyl ether
  15. filtrationThe precipitate was filtered off
  16. customdried

Sources & evidence

ORD record
ord-9360763566c045c3ae1ab4b372b1c1d6
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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