Triethylamine → HCID 25018141, compound

HRID 1878693Notes

Reaction equation

HRID 1878693 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12](=[O:30])[N:13]([CH2:15][CH2:16][O:17][C:18]3[C:27]4[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=4)[N:21]=[CH:20][CH:19]=3)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[C:38](Cl)(=[O:44])[O:39][CH2:40][CH:41]([CH3:43])[CH3:42]>C(Cl)Cl>[CH3:29][O:28][C:24]1[CH:23]=[C:22]2[C:27]([C:18]([O:17][CH2:16][CH2:15][N:13]3[C:12](=[O:30])[CH:11]=[CH:10][C:9]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([NH:1][C:38](=[O:44])[O:39][CH2:40][CH:41]([CH3:43])[CH3:42])[CH:3]=4)=[CH:14]3)=[CH:19][CH:20]=[N:21]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 25018139HCID 25018139, compound

Product 1

HCID 25018141HCID 25018141, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-amino-4-methylphenyl)-1-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridin-2(1H)-one (0.10 g, 0.25 mmol) in 10 mL of CH2Cl2 at rt was added triethylamine (0.083 ml, 0.60 mmol) followed by isobutyl chlorocarbonate (0.048 ml, 0.37 mmol). The reaction was stirred at rt for 4 hours and was then concentrated in vacuo. The residue was dissolved in 50 mL of EtOAc and the resulted organic phase was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine. The organic solution was dried over Na2SO4 and concentrated in vacuo. The residue was washed with 50% hex/EtOAc to give white solid as desired product (0.0879 g, 70% yield). MS (ESI pos. ion) m/z (MH+): 502.1. Calc'd Exact Mass for C29H31N3O5: 501.23.

Workup

  1. concentrationwas then concentrated in vacuo
  2. dissolutionThe residue was dissolved in 50 mL of EtOAc
  3. washthe resulted organic phase was washed with 20 mL of satd
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with 50% hex/EtOAc

Sources & evidence

ORD record
ord-7b6777946ebb4fefb1d55e544a38fe76
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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