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Pyridine → 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide

HRID 218167
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반응식

HRID 218167 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:28])([CH3:27])[C:24](O)=[O:25])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[N:29]1C=CC=CC=1.N1C(F)=NC(F)=NC=1F>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:28])([CH3:27])[C:24]([NH2:29])=[O:25])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 687056802-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanoic acid

생성물 1

HCID 592511432-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(g) 2-(4-(1-(4-Fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanoic acid (50 mg, 0.13 mmol) was dissolved in 5 mL DCM, 32 uL pyridine, and treated with 27 uL cyanuric fluoride. After 1 h, the reaction was extracted from NaHCO3 with EtOAc×3. The combined organic layers were dried over MgSO4, filtered, concentrated and taken up in 2 mL NMP and treated with triethylamine (100 uL) and NH4Cl (50 mg). The reaction was purified by HPLC to give 23 mg of 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide. (M+H)+=382.

후처리

  1. extractionthe reaction was extracted from NaHCO3 with EtOAc×3
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additiontreated with triethylamine (100 uL) and NH4Cl (50 mg)
  6. customThe reaction was purified by HPLC

출처 및 근거

ORD 기록
ord-b218f9866f4140d8bd9e8366eeab46bf
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198311B2

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