Trifluoroacetic acid → 3-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

HRID 883027노트

반응식

HRID 883027 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:27]([N:34]1[CH:38]=[C:37]([C:39]2[C:40](Cl)=[N:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(C(F)(F)F)=O>CCOC(C)=O.O>[CH2:27]([N:34]1[CH:38]=[C:37]([C:39]2[C:40]([O:1][C:2]3[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=3[CH3:20])[C:5]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=3)=[O:6])=[N:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=[N:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 288804893-hydroxy-N-(3-isopropylphenyl)-4-methylbenzamideHCID 866237863-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine

생성물 1

HCID 251022303-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

3-Hydroxy-N-(3-isopropylphenyl)-4-methylbenzamide (100 mg, 0.371 mmol), cesium carbonate (220 mg, 0.676 mmol) and 3-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine (91.0 mg, 0.338 mmol) were combined in an argon-purged sealed tube. DMSO (1.5 mL) was added and the mixture was heated to 130° C. for 23 hours. The cooled reaction was diluted with EtOAc and water and then neutralized with TFA (pH˜7). The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified first by silica gel chromatography (1:1 MTBE/benzene) followed by trituration of the resulting solid with 20:1 hexanes/EtOAc to yield 3-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide as an off-white solid. MS m/z=503 [M+1]+. Calc'd for C32H30N4O2: 502.62.

후처리

  1. custompurged
  2. customsealed tube
  3. additionDMSO (1.5 mL) was added
  4. customThe cooled reaction
  5. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified first by silica gel chromatography (1:1 MTBE/benzene)

출처 및 근거

ORD 기록
ord-62b4752bf96b4874951a3ddd7db92e57
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236823B2

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