Trifluoroacetic acid → N-(4-(2-aminopyridin-4-yloxy)-2-fluorophenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

HRID 476375노트

반응식

HRID 476375 반응식
COC1C=CC(C[NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]4([C:28]([NH:30][C:31]5[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=5)=[O:29])[CH2:27][CH2:26]4)=[O:24])=[C:18]([F:38])[CH:17]=3)[CH:12]=[CH:11][N:10]=2)=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3([C:28]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)=[O:29])[CH2:27][CH2:26]3)=[O:24])=[C:18]([F:38])[CH:17]=2)[CH:12]=[CH:11][N:10]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66604557N-(4-(2-(4-methoxybenzylamino)pyridin-4-yloxy)-2-fluorophenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

생성물 1

HCID 59596943N-(4-(2-aminopyridin-4-yloxy)-2-fluorophenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide수율 42.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of N-(4-(2-(4-methoxybenzylamino)pyridin-4-yloxy)-2-fluorophenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (160 mg, 0.29 mmol) in CH2Cl2 (0.2 mL) was treated with trifluoroacetic acid (0.4 mL, 5.26 mmol) and the resultant mixture was stirred overnight at RT. The reaction mixture was concentrated to dryness and the residue was purified by reverse-phase silica gel chromatography (25-95% acetonitrile in water, 0.1% TFA). The desired fractions were partitioned between saturated aqueous NaHCO3 and EtOAc. The organics were washed with saturated aqueous NaHCO3, water, and brine and were dried over Na2SO4 and concentrated in vacuo to provide N-(4-(2-aminopyridin-4-yloxy)-2-fluorophenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (52 mg, 39% yield). MS (ESI) m/z: 425.1 (M+H+).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was purified by reverse-phase silica gel chromatography (25-95% acetonitrile in water, 0.1% TFA)
  3. customThe desired fractions were partitioned between saturated aqueous NaHCO3 and EtOAc
  4. washThe organics were washed with saturated aqueous NaHCO3, water, and brine
  5. dry with materialwere dried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fb65a14fee9c4a0ca829b9a1e0db0c30
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637672B2

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