HCID 69019986, compound → HCID 69020066, compound

HRID 1865052Notes

Reaction equation

HRID 1865052 reaction equation
[C:1]([C:3]1[C:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:16][CH:15]=2)=[C:5]([C:11]([NH2:13])=[O:12])[N:6]([CH3:10])[C:7]=1[CH2:8][CH3:9])#[N:2]>COC(N(C)C)OC>[CH3:5][N:6]([CH:10]=[N:13][C:11]([C:5]1[N:6]([CH3:10])[C:7]([CH2:8][CH3:9])=[C:3]([C:1]#[N:2])[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)=[O:12])[CH3:7]

Participants

3

Reactant 1

HCID 69019986HCID 69019986, compound

Product 1

HCID 69020066HCID 69020066, compoundYield 190.2%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

Prepare a solution of 4-cyano-3-(2′-cyano-biphenyl-4-yl)-5-ethyl-1-methyl-1H-pyrrole-2 carboxylic acid amide (167 mg, 0.47 mmol, prepared in example Am-3) in 2.5 mL of dry dimethoxymethyl-dimethyl-amine and heat to reflux under nitrogen. After 1 hour allow 1 mL of solvent to distill out of the reaction, then cool the mixture to room temperature. Dilute the slurry with 10 mL of hexanes, filter off the resulting product and wash with 5 mL hexanes. Vacuum-dry the solid overnight to give the title compound (183 mg, 95%). MS(ES+, m/e)=410 (M++1).

Workup

  1. temperatureheat
  2. temperatureto reflux under nitrogen
  3. distillation1 mL of solvent to distill out of the reaction
  4. additionDilute the slurry with 10 mL of hexanes
  5. filtrationfilter off the resulting product
  6. washwash with 5 mL hexanes
  7. customVacuum-dry the solid overnight

Sources & evidence

ORD record
ord-802750aa0ddd469999abd0bcb954507e
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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