Diisopropylethylamine → HCID 58575577, compound

HRID 1189484Notes

Reaction equation

HRID 1189484 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([NH:8][C:9](=[O:23])[C:10]4[N:11]3[C:14]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:15][N:16]=4)=[CH:6][C:5]=2[C:24]([OH:26])=O)[CH2:3][CH2:2]1.BrC1C=C2C(NC(=O)C3N2C(C2CCOCC2)=NN=3)=CC=1C(O)=O.[CH2:51]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:53][NH:52]1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([NH:8][C:9](=[O:23])[C:10]4[N:11]3[C:14]([CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[N:15][N:16]=4)=[CH:6][C:5]=2[C:24]([N:52]2[CH2:53][C:54]3[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:51]2)=[O:26])[CH2:2][CH2:3]1

Participants

8

Reactant 6

HCID 81531DiisopropylethylamineHCID 422478IsoindolineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58575207HCID 58575207, compoundHCID 67133878HCID 67133878, compound

Product 1

HCID 58575577HCID 58575577, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixed liquid of 95.0 mg of a mixture of 8-cyclopropyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid and 8-bromo-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid, 39.0 mg of isoindoline, 190 μL of diisopropylethylamine, and 1.50 mL of N,N-dimethylformamide was added 156 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, followed by stirring at room temperature overnight. To the reaction liquid was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by preparative LC-MS (methanol/0.1% aqueous formic acid solution) to obtain 24.8 mg of 8-cyclopropyl-7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-1-(tetrahydro-2H-pyran-4-yl)[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one as a pale brown solid.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative LC-MS (methanol/0.1% aqueous formic acid solution)

Sources & evidence

ORD record
ord-9b2d3195b1b741488b08338383d21ec9
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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