Tert-Butyl isocyanide → HCID 71187265, compound

HRID 705056Notes

Reaction equation

HRID 705056 reaction equation
[CH:1]([C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][C:4]=1[C:5]([O:7]C)=O)=O.[NH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][N:19]=1.[C:25]([N+:29]#[C-])(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:24][C:22]1[CH:21]=[CH:20][N:19]2[C:18](=[N:17][C:1]3[C:3]4[C:4](=[CH:9][C:10]([O:15][CH3:16])=[CH:11][C:12]=4[O:13][CH3:14])[C:5](=[O:7])[NH:29][C:25]=32)[CH:23]=1

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 521998p-Toluenesulfonic acid monohydrateHCID 5818662-Amino-4-chloropyridineHCID 688335Methyl 2-formyl-3,5-dimethoxybenzoate

Product 1

HCID 71187265HCID 71187265, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under argon, methyl 2-formyl-3,5-dimethoxybenzoate (200 mg, 0.89 mmol) and 2-amino-4-chloropyridine (115 mg, 0.89 mmol) were dissolved in methanol (5 ml), after 5 minutes of stirring at room temperature tert-butylisonitrile (89 mg, 1.07 mmol) was added and after a further 10 minutes of stirring at room temperature 4-toluenesulphonic acid monohydrate (8 mg, 0.05 mmol) was added. The resulting reaction mixture was then stirred at room temperature for 6 h and subsequently concentrated under reduced pressure and taken up in 4 ml of trifluoroacetic acid. The mixture obtained in this manner was stirred at 50° C. for 3 h and then concentrated again, ethanol and water were added to the resulting residue and the pH was then adjusted to 8 using saturated sodium bicarbonate solution. Drying and removal of the resulting precipitate by filtration gave 10-chloro-1,3-dimethoxypyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one in the form of a light-yellow solid (70 mg, 22% of theory). 1H-NMR (400 MHz, d6-DMSO δ, ppm) 13.20 (br. s, 1H, NH), 8.83 (d, 1H), 8.02 (s, 1H), 7.49 (m, 1H), 7.39 (d, 1H), 7.15 (s, 1H), 4.10 (s, 3H), 3.96 (s, 3H).

Workup

  1. additionwas added and after a further 10 minutes
  2. additionwas added
  3. customThe resulting reaction mixture
  4. concentrationsubsequently concentrated under reduced pressure
  5. customThe mixture obtained in this manner
  6. stirringwas stirred at 50° C. for 3 h
  7. concentrationconcentrated again
  8. additionethanol and water were added to the resulting residue
  9. customDrying
  10. customremoval of the resulting precipitate
  11. filtrationby filtration

Sources & evidence

ORD record
ord-a9778c6dcd5d47f7927f067d0c147f65
Source dataset
uspto-grants-2015_11
Patent number
US09173395B2

Reaction notes

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