Pyridine → HCID 86687244, compound

HRID 1402401Notes

Reaction equation

HRID 1402401 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:19])[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[N:8]=2)[N:5]=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=1.N1C=CC=CC=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>C(Cl)Cl.O>[C:34]1([O:33][C:31](=[O:32])[NH:1][C:2]2[N:6]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH3:19])[N:8]=3)[N:5]=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 1049Pyridine3×HCID 15891Phenyl chloroformate3×HCID 86687243HCID 86687243, compound

Product 1

HCID 86687244HCID 86687244, compoundYield 131.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Intermediate 140b (129 mg, 0.41 mmol) in DCM (4.1 mL) was treated with pyridine (0.046 mL, 0.57 mmol) and the mixture was cooled 0° C. Phenyl chloroformate (0.066 mL, 0.53 mmol) was added and the resulting mixture was stirred at RT for 16 h. The mixture was cooled to 0° C. and treated with pyridine (0.013 mL, 0.16 mmol) then phenyl chloroformate (0.015 mL, 0.12 mmol) and stirred at RT for a further 1.75 h. Once again the mixture was cooled to 0° C. and treated with pyridine (0.013 mL, 0.16 mmol) then phenyl chloroformate (0.015 mL, 0.12 mmol) and stirred at RT for 1.75 h. The mixture was diluted with water and the phases were separated. The aqueous layer was extracted with DCM (×2) and the combined organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo to give a yellow gum (236 mg). Trituration with ether and filtration of the resulting solid gave the title compound as a white solid (75 mg, 39%). LCMS (Method 3): Rt 3.21 min, m/z 438.4 [MH+].

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. temperatureOnce again the mixture was cooled to 0° C.
  3. customthe phases were separated
  4. extractionThe aqueous layer was extracted with DCM (×2)
  5. washthe combined organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33fe91c54840403ab7104ab6865b31ec
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…