Trifluoroacetic acid → HCID 178447236, 화합물

HRID 589489노트

반응식

HRID 589489 반응식
[CH:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[N:16][CH:17]=3)[CH:10]=2)[N:5](C2CCCCO2)[N:4]=1)=O.[S].[F:32][C:33]1[CH:34]=[C:35]([C:39]2[C:40]([NH2:46])=[C:41]([NH2:45])[CH:42]=[N:43][CH:44]=2)[CH:36]=[CH:37][CH:38]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(O)CCC>[F:32][C:33]1[CH:34]=[C:35]([C:39]2[C:40]3[N:46]=[C:1]([C:3]4[C:11]5[C:6](=[N:7][CH:8]=[C:9]([C:12]6[CH:13]=[C:14]([NH:18][C:19](=[O:24])[C:20]([CH3:22])([CH3:21])[CH3:23])[CH:15]=[N:16][CH:17]=6)[CH:10]=5)[NH:5][N:4]=4)[NH:45][C:41]=3[CH:42]=[N:43][CH:44]=2)[CH:36]=[CH:37][CH:38]=1

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 5362487SulfurHCID 463121005-(3-Fluorophenyl)pyridine-3,4-diamineHCID 86701079N-(5-(3-formyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)pyridin-3-yl)pivalamide

생성물 1

HCID 178447236HCID 178447236, 화합물수율 72.2%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A solution of N-(5-(3-formyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)pyridin-3-yl)pivalamide (LXV) (75 mg, 0.18 mmol), sulfur (64 mg, 0.20 mmol) and 5-(3-fluorophenyl)pyridine-3,4-diamine (XL) (41 mg, 0.20 mmol) in n-butanol (10 mL) was refluxed overnight under argon. The solution was cooled and filtered and dried under vacuum for 1 h. The residue was taken in dry DCM (5 mL). Triethylsilane (72 μL, 0.45 mmol) followed by TFA (2.5 mL) was added to the solution and stirred for 2 h at room temperature. The solvent was removed under vacuum. Water was added to the residue, sonicated briefly and basified with a 5N NH4OH solution. The solids formed were filtered, washed with cold water and dried at room temperature. The solids were boiled in DCM, cooled to room temperature and sonicated briefly. The solids were filtered, washed with DCM and dried under vacuum to give N-(5-(3-(7-(3-fluorophenyl)-3H-imidazo[4,5-c]pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)pyridin-3-yl)pivalamide (2) as a brown solid (66 mg, 0.13 mmol, 72% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 1.30 (s, 9H), 7.22 (t, 1H), 7.57-7.66 (m, 1H), 8.25 (d, 1H), 8.36 (d, 1H), 8.55 (s, 1H), 8.74 (s, 1H), 8.78 (s, 1H), 8.89 (s, 1H), 8.97 (s, 1H), 9.04 (s, 1H), 9.07 (s, 1H), 9.61 (s, 1H), 13.92 (brs, 1H), 14.63 (brs, 1H); ESIMS found C28H23FN8O m/z 507.5 (M+H).

후처리

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. customdried under vacuum for 1 h
  4. additionwas added to the solution
  5. customThe solvent was removed under vacuum
  6. additionWater was added to the residue
  7. customsonicated briefly
  8. customThe solids formed
  9. filtrationwere filtered
  10. washwashed with cold water
  11. customdried at room temperature
  12. temperaturecooled to room temperature
  13. customsonicated briefly
  14. filtrationThe solids were filtered
  15. washwashed with DCM
  16. customdried under vacuum

출처 및 근거

ORD 기록
ord-386a4c8244074031bf5a1b9f4188a7e6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233104B2

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