HCID 66886373, compound → HCID 58827076, compound

HRID 1877970Notes

Reaction equation

HRID 1877970 reaction equation
[CH2:1]([C:4]1([C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([C:25]#[N:26])=[CH:15][CH:14]=2)[N:9]2[CH:10]=[N:11][CH:12]=[C:8]2[CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].NN.C1COCC1>CCO.[O-]S([O-])(=O)=O.[Cu+2]>[CH2:1]([C:4]1([C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([C:25]#[N:26])=[CH:15][CH:14]=2)[N:9]2[CH:10]=[N:11][CH:12]=[C:8]2[CH2:7][CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 66886373HCID 66886373, compoundHCID 67030329HCID 67030329, compound

Product 1

HCID 58827076HCID 58827076, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-(5-allyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine-5-yl)biphenyl-3-carbonitrile (35 mg, 0.103 mmol) in EtOH (2 mL) at ambient temperature is added H2NNH2/THF (1.0 M, 15 mL, 15 mmol) and saturated aqueous CuSO4 (0.1 mL). The reaction mixture is stirred at ambient temperature overnight. The mixture is concentrated and dissolved in EtOAc, which is washed with water, dried over anhydrous Na2SO4 and concentrated to give the crude oil, which is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 342 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm (HCl salt) 0.95 (t, J=7.2 Hz, 3 H), 1.21-1.33 (m, 2 H), 1.80-1.90 (m, 2 H), 1.90-2.02 (m, 1 H), 2.09-2.37 (m, 3 H), 2.59-2.68 (m, 1 H), 2.71-2.85 (m, 1 H), 6.81-6.88 (m, 1 H), 6.90-6.98 (m, 2 H), 7.19-7.25 (m, 1 H), 7.27-7.39 (m, 3 H), 7.43 (d, J=1.8 Hz, 1 H), 7.71 (dd, J=8.3, 2.0 Hz, 1 H), 8.10-8.18 (m, 1 H).

Workup

  1. concentrationThe mixture is concentrated
  2. dissolutiondissolved in EtOAc
  3. washwhich is washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude oil, which
  7. washeluting with MeOH

Sources & evidence

ORD record
ord-eda7b98b8eed4ee5a27b0db044fc2357
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

Loading…