Pyridine → HCID 86687244, compound

HRID 2282695Notes

Reaction equation

HRID 2282695 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-d20158baf32b41f8b2bf3d958d617307
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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