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Dimethylformamide → 1-(2,4-Dichlorophenyl)-N-(2-(2-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 1478793
ノート
印刷プレビュー

反応式

HRID 1478793 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[N:11]=[N:10]1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:29][C:30]1[C:31](=[O:44])[N:32]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])[N:33]([CH3:36])[C:34]=1[CH3:35].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[C:12]([C:15]([NH:29][C:30]2[C:31](=[O:44])[N:32]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])[N:33]([CH3:36])[C:34]=2[CH3:35])=[O:17])[N:11]=[N:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3021721-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acidHCID 431636614-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one2 回

生成物 1

HCID 118513298
1-(2,4-Dichlorophenyl)-N-(2-(2-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (100 mg, 0.368 mmol), oxalyl chloride (0.048 ml, 0.551 mmol) and DMF (0.057 ml, 0.735 mmol) in DCM (5 ml) was stirred at RT for 15 mins. 4-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (89 mg, 0.404 mmol) was added followed by triethylamine (0.154 ml, 1.103 mmol) and the mixture was stirred at RT for 30 mins. The resulting mixture was diluted with DCM, washed with 0.1M HCl(aq) and sat. NaHCO3(aq) and the organic extracts were passed through a phase separating cartridge and concentrated under reduced pressure. The resultant brown oil was absorbed onto silica and purified by chromatography eluting with 0-10% MeOH in TBME. The product fractions were combined and concentrated under reduced pressure to give a pale pink solid which was triturated with diethylether. The resulting solid was collected by filtration and dried in the vacuum oven to give the title compound as a pale pink solid.

後処理

  1. washwashed with 0.1M HCl(aq) and sat. NaHCO3(aq)
  2. customseparating cartridge
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant brown oil was absorbed onto silica
  5. custompurified by chromatography
  6. washeluting with 0-10% MeOH in TBME
  7. concentrationconcentrated under reduced pressure
  8. customto give a pale pink solid which
  9. customwas triturated with diethylether
  10. filtrationThe resulting solid was collected by filtration
  11. customdried in the vacuum oven

出典と根拠

ORDレコード
ord-9cc27333110747e5a8f13fa4e80620f9
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09403833B2

反応ノート

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