Triethylamine → 5-nitro-1H-pyrazole-3-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-amide

HRID 57795

反応式

HRID 57795 の反応式
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH2:38])=[CH:32][CH:31]=1.CCN=C=NCCCN(C)C>O1CCCC1.O>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH:38][C:9]([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][N:7]=2)=[O:11])=[CH:32][CH:31]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 674302-(4-Chlorophenyl)ethylamineHCID 862226845-Nitro-1H-pyrazole-3-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 1363443545-nitro-1H-pyrazole-3-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-amide収率 43%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-nitro-1H-pyrazole-3-carboxylic acid (200 mg, 1.3 mmol, 1 eq) in tetrahydrofuran (5 mL) were added triethylamine (350 μL, 1.9 mmol, 1.5 eq), hydroxybenzotriazole (HOBT) (257 mg, 1.27 mmol, 1 eq), 2-(4-chloro-phenyl)-ethylamine (180 μL, 1.27 mmol, 1 eq) and EDCI (364 mg, 1.9 mmol, 1.5 eq). The mixture was stirred at room temperature during 20 h. Water (10 mL) was then added and the aqueous phase was extracted with ethyl acetate (2×15 mL). The organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (100/0) to (50/50) to afford 5-nitro-1H-pyrazole-3-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-amide as white solid (160 mg, 43% yield).

後処理

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×15 mL)
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-7a0f096c90634fb5b970bdaed8626bd8
出典データセット
uspto-grants-2016_09
特許番号
US09434745B2

関連ノート

読み込み中…