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Dicyclohexylcarbodiimide → [5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone

HRID 1011903
ノート
印刷プレビュー

反応式

HRID 1011903 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([C:22]([OH:24])=O)[C:17]=1[CH3:25].[N:26]1([CH2:33][CH2:34][OH:35])[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[N:19]=[C:18]([C:22]([N:29]2[CH2:30][CH2:31][CH2:32][N:26]([CH2:33][CH2:34][OH:35])[CH2:27][CH2:28]2)=[O:24])[C:17]=1[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 27365502-(1,4-Diazepan-1-yl)ethan-1-olHCID 673142975-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 67314874[5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone収率 40%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To a suspension of 0.060 g (0.18 mmol) of 5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid in 2 ml of CH2Cl2 was added 0.031 g (0.22 mmol) of 2-(1,4-diazepan-1-yl)ethan-1-ol, diluted in 1.7 ml of CH2Cl2. This solution was treated at 0° C. with 0.048 g (0.23 mmol) of DCC. The reaction was allowed to warm up over night to RT, then partitioned between aqueous saturated NaHCO3/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, dried (Na2SO4) and evaporated. The residue was suspended in EtOAc and filtered to remove the DCC urea. Purification by flash chromatography (SiO2—NH2, n-heptane/EtOAc 1:4) gave 0.033 g (39%) of [5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-[4-(2-hydroxy-ethyl)-[1,4]diazepan-1-yl]-methanone as white oil. MS: 459.3 (MH+).

後処理

  1. custompartitioned between aqueous saturated NaHCO3/EtOAc (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. filtrationfiltered
  6. customto remove the DCC urea
  7. customPurification by flash chromatography (SiO2—NH2, n-heptane/EtOAc 1:4)

出典と根拠

ORDレコード
ord-e741a131714d448195f6d2f35319d480
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977358B2

反応ノート

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