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

HRID 242195

反応式

HRID 242195 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 90.8%

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 (1.00 g, 6.66 mmol) in EtOH (8 mL) was added (4-methoxyphenyl)hydrazine (1.29 g, 9.32 mmol). (Prior to use 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 min. CH2Cl2 was added and the organic phase was washed with 1M 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 (1.38 g, 85%) 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 1M 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-60cd323482e643bdbe1183d98b1166c6
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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