Sodium Bicarbonate → 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide

HRID 58106노트

반응식

HRID 58106 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2.C([O-])(O)=[O:24].[Na+]>C(O)(=O)C.OS(O)(=O)=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:24])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 897829316-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile

생성물 1

HCID 897832376-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide수율 34%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매

실험 절차

6-Methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile (0.02 g, 0.066 mmol) in acetic acid (2 mL) and H2SO4 (2 mL) was stirred at room temperature for 18 hours. The reaction mixture was subsequently poured into a conical flask containing ice and was carefully neutralized with NaHCO3 and extracted into DCM. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with a gradient of 45-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compound as white solid (0.32 g, 34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3H), 7.42 (d, J=1.26 Hz, 1H), 7.73 (br s, 1H), 7.90-8.08 (m, 3H), 8.14 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H11F3N4O, 321.1. found 321.2.

후처리

  1. additionThe reaction mixture was subsequently poured into a conical flask
  2. additioncontaining ice
  3. extractionextracted into DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column)
  7. washeluting with a gradient of 45-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA)

출처 및 근거

ORD 기록
ord-a57eef7e65a748dda85c07464a2797f9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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