HCID 60162558, compound → 4-[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethylamino]-2-methyl-2H-pyridazin-3-one

HRID 243426Notes

Reaction equation

HRID 243426 reaction equation
Cl[C:2]1[CH:7]=[N:6][N:5]([CH3:8])[C:4](=[O:9])[C:3]=1[NH:10][C@H:11]([C:13]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:15]=2[N:14]=1)[CH3:12]>C(OCC)(=O)C.C(=O)([O-])O.[Na+].[Pd]>[F:28][C:25]1[CH:26]=[CH:27][C:15]2[N:14]=[C:13]([C@@H:11]([NH:10][C:3]3[C:4](=[O:9])[N:5]([CH3:8])[N:6]=[CH:7][CH:2]=3)[CH3:12])[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:16]=2[CH:24]=1

Participants

5

Reactant 1

HCID 60162558HCID 60162558, compound

Product 1

HCID 681581204-[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethylamino]-2-methyl-2H-pyridazin-3-oneYield 55%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-Chloro-4-[(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamino]-2-methyl-2H-pyridazin-3-one (0.06 g, 0.15 mmol) in ethyl acetate (5 mL) and sat. aq sodium hydrogen carbonate (1 mL) was hydrogenated over 10% palladium on carbon (20 mg) at room temperature and pressure for 3 h. The reaction mix was filtered, evaporated to dryness and purified by column chromatography (Si—PCC, gradient 50-100% EtOAc in DCM). Fractions containing the product were evaporated and freeze dried to give 326 as a white solid, (30 mg, 55%). LCMS (Method C): RT 4.0 min [M+H]+ 364.09. 1H NMR δ (ppm) (DMSO-d): 7.76 (1H, dd, J=8.83, 4.84 Hz), 7.58-7.56 (5H, m), 7.44 (1H, d, J=4.98 Hz), 7.13 (1H, ddd, J=9.9, 8.9, 2.5 Hz), 6.85 (1H, dd, J=8.90, 2.47 Hz), 6.74 (1H, d, J=7.91 Hz), 5.90 (1H, d, J=5.04 Hz), 4.81 (1H, dq, J=7.12 Hz), 3.59 (3H, s), 1.49 (3H, d, J=6.65 Hz)

Workup

  1. additionThe reaction mix
  2. filtrationwas filtered
  3. customevaporated to dryness
  4. custompurified by column chromatography (Si—PCC, gradient 50-100% EtOAc in DCM)
  5. additionFractions containing the product
  6. customwere evaporated
  7. customfreeze dried

Sources & evidence

ORD record
ord-4494fb491e1d45fa9c7723779613121c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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