HCID 66886373, compound → HCID 58827076, compound

HRID 923289Notes

Reaction equation

HRID 923289 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, 3H), 1.21-1.33 (m, 2H), 1.80-1.90 (m, 2H), 1.90-2.02 (m, 1H), 2.09-2.37 (m, 3H), 2.59-2.68 (m, 1H), 2.71-2.85 (m, 1H), 6.81-6.88 (m, 1H), 6.90-6.98 (m, 2H), 7.19-7.25 (m, 1H), 7.27-7.39 (m, 3H), 7.43 (d, J=1.8 Hz, 1H), 7.71 (dd, J=8.3, 2.0 Hz, 1H), 8.10-8.18 (m, 1H).

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-326ee7d47287447085bd36eba21682cd
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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