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

HRID 58106ノート

反応式

HRID 58106 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a57eef7e65a748dda85c07464a2797f9
出典データセット
uspto-grants-2016_09
特許番号
US09434743B2

反応ノート

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