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

HRID 242175

反応式

HRID 242175 の反応式
C(O[C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH3:5])C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.NN.Cl>CCO>[NH2:10][C:9]1[N:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[N:20]=[C:4]([CH3:5])[C:6]=1[C:7]#[N:8]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 77023(4-Methoxyphenyl)hydrazineHCID 79450(1-Ethoxyethylidene)malononitrile

生成物 1

HCID 671200415-amino-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile収率 81%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
105 °C

実験手順

To a stirred solution of 2-(1-ethoxyethylidene)malononitrile (958 mg, 7.04 mmol) in EtOH (12 mL) was added (4-methoxyphenyl)hydrazine (1.12 g, 8.09 mmol). (Prior to using the hydrazine its HCl salt was washed with NaHCO3/CH2Cl2. The organic phase was concentrated and used directly.) The solution was heated to 105° C. in the microwave for 20 minutes. CH2Cl2 was added and the organic phase was washed with 1 M HCl and 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-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (1.30 g, 81%) which was used as such in the next step. The procedure was adapted from J. Med. Chem. 2004, 47, 5894-5911.

後処理

  1. washwas washed with NaHCO3/CH2Cl2
  2. concentrationThe organic phase was concentrated
  3. additionCH2Cl2 was added
  4. washthe organic phase was washed with 1 M HCl
  5. extractionthe organic extract
  6. washwas washed with aqueous NaHCO3
  7. customThe solution was dried
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-79fa3684f21848b882e7327d35308177
出典データセット
uspto-grants-2014_02
特許番号
US08653112B2

関連ノート

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