Diethyl cyanophosphonate → HCID 67067457、化合物

HRID 599570ノート

反応式

HRID 599570 の反応式
C(P(=O)(OCC)OCC)#N.[CH3:11][O:12][C:13]1[CH:14]=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=O)[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]1.Cl.[NH2:31][CH2:32][C:33](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][C:33](=[O:42])[CH2:32][NH:31][C:27](=[O:29])/[CH:26]=[CH:25]/[C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[C:13]([O:12][CH3:11])[CH:14]=2)=[CH:40][CH:39]=1

参加物

8

反応物 4

HCID 76257Diethyl cyanophosphonateHCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 86585896Sodium bicarbonate water

生成物 1

HCID 67067457HCID 67067457、化合物収率 13.6%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Diethyl cyanophosphonate (0.12 mL) was added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (200 mg) and triethylamine (0.54 mL) in DMF (2 mL), and the reaction solution was stirred at 0° C. for 30 minutes. A solution of 1-amino-3-(4-fluorophenyl)propan-2-one hydrochloride (CAS #93102-98-8, 158 mg) in DMF (1 mL) was added dropwise to the reaction solution over 20 minutes, and the reaction solution was stirred at 0° C. for 1.5 hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1) to obtain 43 mg of the title compound. The property values of the compound are as follows.

後処理

  1. stirringthe reaction solution was stirred at 0° C. for 1.5 hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1)

出典と根拠

ORDレコード
ord-c90514c1d38044b2b9e0d225f94b4341
出典データセット
uspto-grants-2011_03
特許番号
US07897632B2

反応ノート

読み込み中…