Trifluoroacetic acid → 5-(5-fluoropyridin-3-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide

HRID 2367704노트

반응식

HRID 2367704 반응식
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C2CCCCO2)[N:19]=[C:18]3[C:30]([NH:32][C:33]2[CH:34]=[N:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=2)=[O:31])[CH:12]=[N:13][CH:14]=1.C([SiH](CC)CC)C>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:30]([NH:32][C:33]2[CH:34]=[N:35][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:37][CH:38]=2)=[O:31])[CH:12]=[N:13][CH:14]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 866796995-(5-fluoropyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide

생성물 1

HCID 866797005-(5-fluoropyridin-3-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (10 mL) was added to a solution of 5-(5-fluoropyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide (CXXX) (0.420 g, 0.86 mmol) and triethylsilane (0.345 mL, 2.16 mmol) in DCM (10 mL) and stirred 5 h at room temperature. The solvent was removed under vacuum. The residue was treated with water, sonicated briefly to disperse the solids, basified to pH 9.0 with 5 N NH4OH and sonicated again. The solids were filtered, washed with cold water and air dried at room temperature. The solids were suspended in DCM:MeOH (1:1) mixture and boiled to get a clear solution. The solution was cooled to room temperature. The solids formed were filtered washed with DCM and dried under vacuum at room temperature to get 5-(5-fluoropyridin-3-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide (2) as a white solid (72.9 mg, 0.18 mmol, 21% yield). 1H NMR (DMSO-d6) δ ppm 14.13 (br. s, 1H), 11.11 (s, 1H), 9.27 (d, J=1.8 Hz, 1H), 8.84 (m, 1H), 8.63 (dd, J=6.8, 1.8 Hz, 1H), 8.60 (d, J=2.0 Hz, 1H), 8.53 (m, 1H), 8.14-8.11 (m, 1H), 7.94 (d, J=6.9 Hz, 1H), 7.90-7.83 (m, 2H); ESIMS found for C19H11F4N5O m/z 402.30 (M+H).

후처리

  1. customThe solvent was removed under vacuum
  2. additionThe residue was treated with water
  3. customsonicated briefly
  4. additionto disperse the solids
  5. customsonicated again
  6. filtrationThe solids were filtered
  7. washwashed with cold water and air
  8. customdried at room temperature
  9. customto get a clear solution
  10. temperatureThe solution was cooled to room temperature
  11. customThe solids formed
  12. filtrationwere filtered
  13. washwashed with DCM
  14. customdried under vacuum at room temperature

출처 및 근거

ORD 기록
ord-0431fa96c50e4e57af851bc014d998ab
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697887B2

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