Methylamine → HCID 68155867, compound

HRID 242203Notes

Reaction equation

HRID 242203 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:14]([C:15](=O)[CH:16]([CH3:20])[CH2:17][CH:18]=O)=[C:13]([C:22]#[N:23])[C:12]([CH3:24])=[N:11]1.[CH3:25][NH2:26]>C(Cl)Cl>[CH3:25][N:26]1[CH:18]=[CH:17][C:16]([CH3:20])=[C:15]1[C:14]1[N:10]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[F:1])[N:11]=[C:12]([CH3:24])[C:13]=1[C:22]#[N:23]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86668981HCID 86668981, compound

Product 1

HCID 68155867HCID 68155867, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(2-fluoro-4-methoxyphenyl)-3-methyl-5-(2-methyl-4-oxobutanoyl)-1H-pyrazole-4-carbonitrile (29 mg, 0.09 mmol) in CH2Cl2 (2 mL) was added methylamine (2.0 M solution in methanol, 0.61 mL, 1.2 mmol) at ambient temperature in a closed microwave tube. The reaction mixture was stirred at ambient temperature for 14 h and 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 5-(1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (20 mg, 62%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-8f52529b749044638e5b26a6c9221159
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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