Hydrochloric Acid → HCID 67120069, compound

HRID 1410155Notes

Reaction equation

HRID 1410155 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH:5]([CH3:25])[C:6]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:11]=[C:10]([CH2:21][CH3:22])[C:9]=1[C:23]#[N:24])=O.CN.Cl.O>CO.C(Cl)Cl>[CH2:21]([C:10]1[C:9]([C:23]#[N:24])=[C:8]([C:6]2[O:2][CH:3]=[CH:4][C:5]=2[CH3:25])[N:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[N:11]=1)[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 6329Methylamine2×HCID 67120059HCID 67120059, compound

Product 1

HCID 67120069HCID 67120069, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(4,4-dimethoxy-2-methylbutanoyl)-3-ethyl-1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (20 mg, 0.05 mmol) in MeOH (1.5 mL) were added methylamine (2.0 M solution in methanol, 0.20 mL, 0.4 mmol) and cone. HCl (0.1 mL) at ambient temperature in a closed microwave tube. The reaction mixture was stirred at ambient temperature for 14 h then additional methylamine (2.0 M solution in methanol, 2.70 mL, 5.4 mmol) and cone. HCl (0.3 mL) were added and the reaction was heated to 80 C. for 14 hours. Water and CH2Cl2 was added, the phases separated and the organic phase was concentrated under reduced pressure. Purification using a silica plug (heptane/CH2Cl2/Et2O-1:0:0-1:1:0-0:1:0-0:1:1) yielded 3-ethyl-1-(4-methoxyphenyl)-5-(3-methylfuran-2-yl)-1H-pyrazole-4-carbonitrile (5 mg, 0.02 mmol, 30%).

Workup

  1. customat ambient temperature
  2. temperaturethe reaction was heated to 80 C
  3. waitfor 14 hours
  4. customthe phases separated
  5. concentrationthe organic phase was concentrated under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-2aada305cde341bbaccfbacc17f59fa2
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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