Diisopropylethylamine → HCID 89702383, compound

HRID 2202971Notes

Reaction equation

HRID 2202971 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:34][C:33]2=[O:46])=[CH:28][C:27]=1[NH:47][CH3:48].[CH3:49][O:50][C:51]([CH:53]1[CH2:55][CH:54]1[C:56](O)=O)=[O:52].C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH2:39]([O:38][C:35]1[CH:36]=[CH:37][N:32]([C:29]2[CH:30]=[CH:31][C:26]3[N:25]=[C:56]([CH:54]4[CH2:55][CH:53]4[C:51]([O:50][CH3:49])=[O:52])[N:47]([CH3:48])[C:27]=3[CH:28]=2)[C:33](=[O:46])[CH:34]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 125109711-Ethoxycarbonylcyclopropanecarboxylic acidHCID 89690567HCID 89690567, compound

Product 1

HCID 89702383HCID 89702383, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (4.97, g) was added to a solution of 1-(4-amino-3-(methylamino)phenyl)-4-(benzyloxy)pyridin-2(1H)-one (3.5 g), (1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid (1.884 g) and N,N-diisopropylethylamine (3.80 ml) in DMF (70 ml) at room temperature. The mixture was stirred at room temperature for 1 h. To the resulting mixture was added water, and the resulting precipitate was collected by filtration and washed with water and IPA. The obtained solid was dissolved in AcOH (35 ml). The mixture was stirred at 80° C. for 1 h. After evaporation of the mixture, the residue was diluted with saturated NaHCO3 solution and EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was washed with IPE to give the title compound (2.9 g) as a pink solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water and IPA
  3. dissolutionThe obtained solid was dissolved in AcOH (35 ml)
  4. stirringThe mixture was stirred at 80° C. for 1 h
  5. customAfter evaporation of the mixture
  6. additionthe residue was diluted with saturated NaHCO3 solution and EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. washThe residue was washed with IPE

Sources & evidence

ORD record
ord-76d09b63efba48ddbf8cb42b04cc9b83
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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