4-Cyanobenzaldehyde → HCID 25015937, compound

HRID 1785612Notes

Reaction equation

HRID 1785612 reaction equation
Cl.[NH2:2][N:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=2)[N:5]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:4]1=[O:26].[C:27]([C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1)#[N:28].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>O.C(OCC)(=O)C.C(O)(=O)C.C1COCC1>[C:27]([C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:2][N:3]2[CH2:7][CH:6]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=3)[N:5]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[C:4]2=[O:26])=[CH:31][CH:30]=1)#[N:28]

Participants

9

Reactant 4

HCID 660424-CyanobenzaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 68427637HCID 68427637, compound

Product 1

HCID 25015937HCID 25015937, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-amino-3-[2-(4-methoxy-phenyl)ethyl]-4-(3,4-dimethylphenyl)-2-imidazolidinone hydrochloride (350 mg, 0.93 mmol), THF (4.5 mL), and 4-cyanobenzaldehyde (131 mg, 1.0 mmol) is stirred at 50° C. for 30 minutes, then cooled in an ice bath and glacial acetic acid (3.5 mL) is added. To the resulting mixture is added NaCNBH3 (183 mg, 2.9 mmol). The reaction is stirred in the cold for 2 hours and ethyl acetate and H2O are added. The mixture is made basic with solid NaHCO3, and the organic phase is washed with 10% aqueous NaHCO3 and brine. The organic phase is dried (Na2SO4) and concentrated under reduced pressure. The residue is purified over silica (45% ethyl acetate/hexanes) to afford 167 mg (40% yield) of the desired product. 1H NMR (CDCl3) δ 7.65 (m, 2H), 7.56 (d, J=8.4 Hz, 2H), 7.12 (d, J=7.8 Hz, 1H), 7.05 (m, 2H), 6.89 (m, 2H), 6.84 (m, 2H), 4.20 (m, 3H), 3.82 (s, 3H), 3.67 (m, 1H), 3.48 (t, J n=8.4 Hz, 1H), 3.06 (t, J=8.1 Hz, 1H), 2.91 (m, 1H), 2.76 (m, 1H), 2.67 (m, 1H), 2.29 (s, 3H), 2.26 (s, 3H). MS 455 (MH+). Anal. Calcd. For C28H30N4O2: C, 73.98, H, 6.65; N, 12.33. Found: C, 73.68, H, 6.65; N, 12.08.

Workup

  1. temperaturecooled in an ice bath
  2. washthe organic phase is washed with 10% aqueous NaHCO3 and brine
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified over silica (45% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-26b9fe0e3007440bab82313a178aeab4
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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