1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole

HRID 1941887노트

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HRID 1941887 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.CC[N:21]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[O:40]1[CH2:44][CH2:43][O:42][CH:41]1[C:45]1[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][CH:46]=1>CN(C=O)C>[O:40]1[CH2:44][CH2:43][O:42][CH:41]1[C:45]1[CH:52]=[CH:51][C:48]([C:49]2[N:21]=[C:16]([C:10]3[CH:9]=[N:8][N:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[C:11]=3[C:12]([F:13])([F:14])[F:15])[O:18][N:50]=2)=[CH:47][CH:46]=1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileHCID 167877231-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 669966503-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
140 °C

실험 절차

To a solution of 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (31.46 g, 122 mmol) in DMF (200 mL) was added EDCI (23.34 g, 134 mmol) and HOBt (16.53 g, 122 mmol). After the reaction was stirred for 30 min. at room temperature 4-(1,3-dioxolan-2-yl)benzonitrile, Int.6-A, (16.53 g, 122 mmol) was added. The reaction mixture was stirred at 140° C. for 4 hr. The reaction mixture was concentrated under reduced pressure to remove the volatiles. The residue was partitioned between water and ethyl acetate and the organic layer was washed with aq. HCl solution, NaHCO3 solution, water, and brine before being dried over Na2SO4 and concentrated to provide 3-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole (25 g, 58 mmol). The compound had an HPLC retention time=6.15 min. −Column: HYPERSIL® BDS C18 (4.6×50 mm) Flow rate=0.8 mL/min. Solvent A=, 0.1% TFA in water; Solvent B=acetonitrile. 5%-100% B (0-6 min), 100% B (6-9 min), 100%-5% B (9-11 min). LC/MS M+1=430.0.

후처리

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove the volatiles
  4. customThe residue was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with aq. HCl solution, NaHCO3 solution, water, and brine
  6. dry with materialbefore being dried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-52e85c73cce64fa2971456a0772dae4b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389509B2

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