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

반응식

HRID 1011903 반응식
[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]

참가 물질

5

반응물 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

생성물 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]-methanone수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-e741a131714d448195f6d2f35319d480
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977358B2

연결된 노트

불러오는 중…