Diisopropylethylamine → HCID 56928713, compound

HRID 1396675Notes

Reaction equation

HRID 1396675 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][C:7]([O:15][CH2:16][CH:17]3[CH2:21][CH2:20][O:19][CH2:18]3)=[C:8]([C:12]([OH:14])=O)[CH:9]=2)[N:4]2[C:22]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:23][CH:24]=[C:3]12.[Br:31][C:32]1[CH:33]=[C:34]2[CH2:40][CH2:39][NH:38][C:35]2=[N:36][CH:37]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:31][C:32]1[CH:33]=[C:34]2[CH2:40][CH2:39][N:38]([C:12]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][C:7]=3[O:15][CH2:16][CH:17]3[CH2:21][CH2:20][O:19][CH2:18]3)[N:4]3[C:22]([CH:25]5[CH2:26][CH2:27][O:28][CH2:29][CH2:30]5)=[N:23][CH:24]=[C:3]3[C:2](=[O:1])[NH:11]4)=[O:14])[C:35]2=[N:36][CH:37]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219640795-Bromo-2,3-dihydro-7-azaindoleHCID 66696216HCID 66696216, compound

Product 1

HCID 56928713HCID 56928713, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 150 mg of 4-oxo-8-(tetrahydrofuran-3-ylmethoxy)-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid and 3 mL of N,N-dimethyl formamide were sequentially added 122 mg of 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, 0.25 mL of N,N-diisopropylethylamine, and 220 mg of HATU, followed by stirring at room temperature for 72 hours. The mixture was poured into a cooled saturated aqueous sodium hydrogen carbonate solution, followed by stirring for 30 minutes and extracting with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=100/0-92/8) to obtain 81 mg of 7-[(5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)carbonyl]-8-(tetrahydrofuran-3-ylmethoxy)-1-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]quinoxalin-4(5H)-one as a white solid.

Workup

  1. stirringby stirring for 30 minutes
  2. extractionextracting with ethyl acetate
  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 silica gel column chromatography (chloroform/methanol=100/0-92/8)

Sources & evidence

ORD record
ord-bf4c2aa9cdd14cfe852a0108ffcfee95
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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