Ammonium → 6-[Amino-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one

HRID 2298989Notes

Reaction equation

HRID 2298989 reaction equation
Cl[C:2]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)([C:25]1[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:8](=[O:17])[CH:7]=[C:6]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Cl)[CH:19]=1.[ClH:38].[NH4+:39]>C1COCC1>[NH2:39][C:2]([C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)([C:25]1[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:8](=[O:17])[CH:7]=[C:6]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:38])[CH:19]=1

Participants

5

Reactant 3

HCID 223AmmoniumHCID 313Hydrochloric AcidHCID 183790276-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one

Product 1

HCID 98498776-[Amino-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one; hydrochloride (2.15 g, 3.7 mmol) in THF (40 mL) was treated with ammonium, stirred at ambient temperature for 2 hours, and concentrated in vacuo. The reaction mixture was diluted with ethyl acetate/H2O (1:1, 200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (200 mL), dried (MgSO4), filtered, and concentrated in vacuo to give a crude yellow foam. Purification by flash column chromatography (silica, EtOAc:MeOH:NEt3 9:1:.01) gave 6-[Amino-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one (1.54 g, 79%) as a yellow foam.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe reaction mixture was diluted with ethyl acetate/H2O (1:1, 200 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic extracts were washed with brine (200 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude yellow foam
  9. customPurification by flash column chromatography (silica, EtOAc:MeOH:NEt3 9:1:.01)

Sources & evidence

ORD record
ord-b0f71bbb55dd4d9498ce1fe4c931fd9e
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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