Trifluoroacetic acid → HCID 178460086、化合物

HRID 2178645ノート

反応式

HRID 2178645 の反応式
[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:22])[CH2:20][CH3:21])[CH:15]=[N:16][CH:17]=3)[CH:10]=2)[N:5](C2CCCCO2)[N:4]=1)=O.[S].[N:30]1[CH:35]=[C:34]([NH2:36])[C:33]([NH2:37])=[C:32]([C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)[CH:31]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>CN(C=O)C>[N:40]1[CH:41]=[CH:42][CH:43]=[C:38]([C:32]2[C:33]3[N:37]=[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:22])[CH2:20][CH3:21])[CH:15]=[N:16][CH:17]=6)[CH:10]=5)[NH:5][N:4]=4)[NH:36][C:34]=3[CH:35]=[N:30][CH:31]=2)[CH:39]=1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 5362487SulfurHCID 46315401[3,3'-Bipyridine]-4,5-diamineHCID 58377773N-(5-(3-formyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)pyridin-3-yl)propionamide

生成物 1

HCID 178460086HCID 178460086、化合物収率 49%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-(5-(3-formyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)pyridin-3-yl)propionamide (LX) (1 eq), sulfur (1 eq) and 3,3′-bipyridine-4,5-diamine (XLVIII) (1 eq) in DMF was heated overnight at 140° C. under argon. The solution was cooled and the DMF was distilled under vacuum. The residue was taken in DCM. Triethylsilane (2.5 eq) followed by TFA (30% by volume) was added to the solution and stirred for 2 h at room temperature until TLC showed disappearance of starting material. The solvent was removed under vacuum. Water was added to the residue, sonicated briefly and basified with 5 N NH4OH solution. The solids formed were filtered, washed with cold water and dried at room temperature. The solids were triturated with DCM followed by MeOH to get N-(5-(3-(7-(pyridin-3-yl)-3H-imidazo[4,5-c]pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)pyridin-3-yl)propionamide (47) as a brown solid (49% yield). 1H NMR (DMSO-d6, 400 MHz): δ 1.67 (t, J=6 Hz, 3H), 2.45 (q, J=6 Hz, 2H), 7.62 (m, 1H), 8.50 (s, 1H), 8.62 (m, 1H), 8.72 (s, 1H), 8.77 (m, 3H), 8.91 (m, 1H), 8.99 (m, 2H), 9.41 (s, 1H), 10.31 (s, 1H), 13.95 (s, 1H), 14.62 (s, 1H). ESIMS found C25H19N9O m/z 462.50 (M+H).

後処理

  1. temperatureThe solution was cooled
  2. distillationthe DMF was distilled under vacuum
  3. additionwas added to the solution
  4. customThe solvent was removed under vacuum
  5. additionWater was added to the residue
  6. customsonicated briefly
  7. customThe solids formed
  8. filtrationwere filtered
  9. washwashed with cold water
  10. customdried at room temperature
  11. customThe solids were triturated with DCM

出典と根拠

ORDレコード
ord-e5aaaeb1365c48f09dbafec6439b403e
出典データセット
uspto-grants-2015_06
特許番号
US09067939B2

反応ノート

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