2-Nitrobenzoyl chloride → 3-(2-Nitro-benzoylamino)-thieno[2,3-c]pyrazole-1,5-dicarboxylic Acid 5-tert-butyl Ester 1-ethyl Ester

HRID 549429

反応式

HRID 549429 の反応式
[NH2:1][C:2]1[C:3]2[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[S:12][C:4]=2[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(N(C(C)C)CC)(C)C.[N+:31]([C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37])([O-:33])=[O:32]>O1CCCC1>[CH2:10]([O:9][C:7]([N:5]1[C:4]2[S:12][C:13]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])=[CH:14][C:3]=2[C:2]([NH:1][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=2[N+:31]([O-:33])=[O:32])=[N:6]1)=[O:8])[CH3:11]

参加物

5

反応物 3

HCID 118752-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 577372725-tert-butyl 1-ethyl 3-amino-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate

生成物 1

HCID 577372653-(2-Nitro-benzoylamino)-thieno[2,3-c]pyrazole-1,5-dicarboxylic Acid 5-tert-butyl Ester 1-ethyl Ester収率 69.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-tert-butyl 1-ethyl 3-amino-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate (500 mg, 1.606 mmol) and diisopropylethylamine (DIEA, 0.824 mL, 4.818 mmol) in tetrahydrofuran (THF, 20 mL) at 0° C., 2-nitro-benzoyl chloride (0.318 mL, 2.409 mmol) was added. The reaction mixture was kept at the same temperature for 10 minutes then allowed to reach room temperature and let react overnight. The solvent was removed under vacuum, the residue was dissolved in dichloromethane (DCM) and washed with a 10% solution of acetic acid (AcOH), water, saturated NaHCO3 and brine. The crude was purified on silica gel (eluant dichloromethane/methanol 96/4) yielding 512 mg (69%) of the title compound.

後処理

  1. customto reach room temperature
  2. customlet react overnight
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane (DCM)
  5. washwashed with a 10% solution of acetic acid (AcOH), water, saturated NaHCO3 and brine
  6. customThe crude was purified on silica gel (eluant dichloromethane/methanol 96/4)

出典と根拠

ORDレコード
ord-3a9d4cf274c4427fa0a0dc9f7027a263
出典データセット
uspto-grants-2011_05
特許番号
US07943654B2

関連ノート

読み込み中…