1,2-Dichloroethane → HCID 60736795, compound

HRID 526417Notes

Reaction equation

HRID 526417 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[NH2:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([C:12]#[N:11])=[CH:14][CH:15]=2)=[O:8])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 792226-Chloronicotinic acidHCID 81531Diisopropylethylamine2×HCID 826084-(Aminomethyl)benzonitrile2×

Product 1

HCID 60736795HCID 60736795, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combined 6-chloronicotinic acid (1.0 g, 6.35 mmol), 4-(aminomethyl)benzonitrile (1.007 g, 7.62 mmol), and EDC (1.825 g, 9.52 mmol) in methylene chloride (50 mL) then added Hunig's base (2.328 mL, 13.33 mmol) and the mixture stirred at 20° C. for 2 h. More 4-(aminomethyl)benzonitrile (250 mg), EDC (750 mg) and Hunig's base (1 mL) was added and stirring continued for 2 days. The reaction was concentrated in vacuo to give a residue which was taken up in EtOAc (100 mL) and washed with saturated aqueous ammonium chloride (100 mL) and brine, dried over magnesium sulfate and concentrated in vacuo to give a residue which was purified on an 80 g silica gel column eluted with 0 to 80% EtOAc in hexanes to give the title compound (1.1 g, 63.8% yield) as a white solid. MS m/z 272, 274 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.58 (d, J=6.1 Hz, 2H) 7.53 (d, J=8.6 Hz, 2H) 7.68 (dd, J=8.3, 0.8 Hz, 1H) 7.77-7.85 (m, 2H) 8.28 (dd, J=8.3, 2.5 Hz, 1H) 8.89 (dd, J=2.5, 0.5 Hz, 1H) 9.40 (t, J=5.7 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto give a residue which
  3. washwashed with saturated aqueous ammonium chloride (100 mL) and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified on an 80 g silica gel column
  8. washeluted with 0 to 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-aea6e34bb8604e8bb4a1f2c5c1cc7f5b
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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