Hydrochloric Acid → HCID 67120069, compound

HRID 242207Notes

Reaction equation

HRID 242207 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 conc. 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 conc. HCl (0.3 mL) were added and the reaction was heated to 8° 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. temperaturethe reaction was heated to 8° C. for 14 hours
  2. customthe phases separated
  3. concentrationthe organic phase was concentrated under reduced pressure
  4. customPurification

Sources & evidence

ORD record
ord-e20aa49f533047d5a48e6522a28510e7
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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