Hydrochloric Acid → 5-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 242191

Reaction equation

C(O[C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH3:5])C.[F:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[NH:20][NH2:21].C(Cl)Cl.Cl>CCO>[NH2:10][C:9]1[N:20]([C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[F:11])[N:21]=[C:4]([CH3:5])[C:6]=1[C:7]#[N:8]

Participants

Conditions

Temperature: 105 °C

Procedure

To a stirred solution of 2-(1-ethoxyethylidene)malononitrile (167 mg, 1.23 mmol) was added (2-fluoro-4-methoxyphenyl)hydrazine (220 mg, 1.41 mmol) in EtOH (3 mL). The solution was heated to 105° C. in the microwave for 30 min. CH2Cl2 and 1 M HCl was added and separated, the organic extract was washed with aqueous NaHCO3. The solution was dried using a phase separator and concentrated under reduced pressure to give 5-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (256 mg, 85%), which was used in the next step without further purification.

Workup

customseparated
extractionthe organic extract
washwas washed with aqueous NaHCO3
customThe solution was dried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2e7aadd7785c430dac02e54b8518cf76
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653112B2

Linked notes

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