1,2-Dichloroethane → (4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

HRID 1941884노트

반응식

HRID 1941884 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[CH:9]=[N:8]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.O[NH:43][C:44](=[NH:53])[C:45]1[CH:50]=[CH:49][C:48]([CH2:51][OH:52])=[CH:47][CH:46]=1.Cl>CN(C=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]2[O:18][N:53]=[C:44]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][OH:52])=[CH:47][CH:46]=3)[N:43]=2)[CH:9]=[N:8]1

참가 물질

9

반응물 6

HCID 111,2-Dichloroethane2회HCID 313Hydrochloric AcidHCID 757711-Hydroxybenzotriazole2회HCID 81531Diisopropylethylamine2회HCID 167877231-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 178513316HCID 178513316, 화합물

생성물 1

HCID 66996907(4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol수율 58%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (2.57 g, 9.99 mmol) in DMF (30 mL) was added EDC (2.395 g, 12.49 mmol), HOBt (1.913 g, 12.49 mmol) and Hunig's Base (5.24 mL, 30.0 mmol). The reaction was stirred for 40 min. at room temperature, then N-hydroxy-4-(hydroxymethyl)benzimidamide, Int.2, (2.076 g, 12.49 mmol) was added. The reaction mixture was stirred at room temperature for 7 h, then additional EDC (2.395 g, 12.49 mmol), HOBt (1.913 g, 12.49 mmol) and Hunig's Base (5.24 mL, 30.0 mmol) were added. The reaction was heated to 60° C. for 2 h, then at 110° C. for 10 min. 1N aq. HCl was added to adjust the pH to 1, then 30 mL of water was added. The resulting precipitated product was collected by filtration and washed with water to afford (4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (2.28 g, 5.83 mmol, 58%) as a light yellow solid.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 7 h
  2. temperatureThe reaction was heated to 60° C. for 2 h
  3. waitat 110° C. for 10 min
  4. customThe resulting precipitated product
  5. filtrationwas collected by filtration
  6. washwashed with water

출처 및 근거

ORD 기록
ord-8051eedff57d4b2a9774cd314f2cbe34
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389509B2

반응 노트

불러오는 중…