Benzoic Acid → HCID 67977238、化合物

HRID 2168192ノート

反応式

HRID 2168192 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][CH3:39])[CH2:34][CH2:33]1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(N(CC)CC)C.[C:47](O)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[CH3:39][N:38]([C:47]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:54])[CH:35]1[CH2:36][CH2:37][N:32]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:33][CH2:34]1

参加物

6

反応物 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

生成物 1

HCID 67977238HCID 67977238、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a round bottomed flask benzoic acid (0.627 g, 5.13 mmol, commercially available from e.g. Sigma-Aldrich) and HATU (2.129 g, 5.60 mmol) were dissolved in DCM (10 mL). The reaction mixture was stirred at room temperature for 30 minutes before 1-boc-4-methylaminopiperidine (1 g, 4.67 mmol, commercially available from e.g. Apollo, Fluorochem or Astatech) was added followed by triethylamine (1.626 mL, 11.67 mmol). The reaction was stirred at room temperature overnight. Solvent was removed in vacuo and the crude dissolved in DCM then organic phase was extracted with a saturated NaHCO3 solution (twice), a 10% citric acid solution (twice) then washed with brine and dried over MgSO4. Solvent was removed in vacuo and the crude purified on a silica column (40+M) eluting with DCM/MeOH; 90/10. Fractions containing desired compound were joined and solvents were removed in vacuo, to give title compound D14 as a pale yellow oil in 1.66 g. LCMS [M+H]+319.13 [M+H-tBu][email protected] min (2 min run)

後処理

  1. additioncommercially available from e.g. Apollo, Fluorochem or Astatech) was added
  2. customSolvent was removed in vacuo
  3. dissolutionthe crude dissolved in DCM
  4. extractionorganic phase was extracted with a saturated NaHCO3 solution (twice), a 10% citric acid solution (twice)
  5. washthen washed with brine
  6. dry with materialdried over MgSO4
  7. customSolvent was removed in vacuo
  8. customthe crude purified on a silica column (40+M)
  9. washeluting with DCM/MeOH
  10. additionFractions containing desired compound
  11. customsolvents were removed in vacuo

出典と根拠

ORDレコード
ord-9a017cd384b744749136970c7679af96
出典データセット
uspto-grants-2015_06
特許番号
US09045485B2

反応ノート

読み込み中…