Isobutyric Acid → HCID 83449983, compound

HRID 2202869Notes

Reaction equation

HRID 2202869 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[C:11](O)(=O)[CH:12]([CH3:14])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[Cl-].[Ca+2].C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[N:8]([CH3:9])[C:6]=2[CH:7]=1

Participants

7

Reactant 5

HCID 6590Isobutyric AcidHCID 81531DiisopropylethylamineHCID 5284359Calcium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 121982705-Bromo-N1-methylbenzene-1,2-diamine

Product 1

HCID 83449983HCID 83449983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (122 mg) and isobutyric acid (0.056 ml) in DMF (2 ml) was added HATU (242 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. After being stirred, N,N-diisopropylethylamine (0.311 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was stirred in AcOH (2.00 ml) at 90° C. for 1 h and at room temperature overnight. The mixture was quenched with saturated NaHCO3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (119 mg) as a pale yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. stirringThe resulting residue was stirred in AcOH (2.00 ml) at 90° C. for 1 h and at room temperature overnight
  9. customThe mixture was quenched with saturated NaHCO3 solution at room temperature
  10. extractionextracted with EtOAc
  11. customThe organic layer was separated
  12. washwashed with water and brine
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated in vacuo
  15. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-093fb1ed00db4bc8b25d1d9cc45d7a46
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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