Benzoic Acid → HCID 67977238, compound

HRID 2168192Notes

Reaction equation

HRID 2168192 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 67977238HCID 67977238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-9a017cd384b744749136970c7679af96
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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