Diisopropylethylamine → HCID 86679264, compound

HRID 1519693Notes

Reaction equation

HRID 1519693 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:35]([O:42][NH2:43])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:44]([C:47]([N:53]([CH3:68])[C:54]([C:56]1[CH:61]=[CH:60][C:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:58][CH:57]=1)=[O:55])([CH3:52])[C:48]([NH:50][CH3:51])=[O:49])(O)=[O:45].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:35]([O:42][NH:43][C:44](=[O:45])[C:47]([N:53]([C:54]([C:56]1[CH:57]=[CH:58][C:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:60][CH:61]=1)=[O:55])[CH3:68])([CH3:52])[C:48]([NH:50][CH3:51])=[O:49])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71268205HCID 71268205, compound

Product 1

HCID 86679264HCID 86679264, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.30 mL), HATU (0.35 g) and O-benzylhydroxylamine hydrochloride (0.14 g) were added in this order, under ice cooling, to a DMF (5.0 mL) solution of 4-{[2-carboxy-1-(methylamino)-1-oxopropan-2-yl](methyl)carbamoyl}biphenyl (0.23 g) as obtained in Example 12-(2), and the mixture was stirred for 1 hour under ice cooling and for 3 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, whereafter the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=70/30→0/100) and (gradient elution with chloroform/methanol=98/2→95/5) to obtain N-(benzyloxy)-2-[(biphenyl-4-ylcarbonyl)(methyl)amino]-N′,2-dimethylpropanediamide (light brown oil) (0.22 g, 75%).

Workup

  1. customas obtained in Example 12-(2)
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, whereafter the desiccant
  4. filtrationwas filtered out
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=70/30→0/100) and (gradient elution with chloroform/methanol=98/2→95/5)

Sources & evidence

ORD record
ord-8800f16e366642fe821aa60e6243b8bd
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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