Diisopropylethylamine → HCID 56928812, compound

HRID 1396677Notes

Reaction equation

HRID 1396677 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:21])[C:8]3[N:9]2[C:12]([CH:15]2[CH2:20][CH2:19][CH2:18][O:17][CH2:16]2)=[N:13][CH:14]=3)=[CH:4][C:3]=1[C:22](O)=[O:23].[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[CH2:35][CH2:34][NH:33][C:30]2=[CH:31][N:32]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O.CN(C)C=O>[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[CH2:35][CH2:34][N:33]([C:22]([C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[CH3:1])[N:9]3[C:12]([CH:15]5[CH2:20][CH2:19][CH2:18][O:17][CH2:16]5)=[N:13][CH:14]=[C:8]3[C:7](=[O:21])[NH:6]4)=[O:23])[C:30]2=[CH:31][N:32]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 234340355-Methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridineHCID 58574974HCID 58574974, compound

Product 1

HCID 56928812HCID 56928812, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 200 mg of 8-methyl-4-oxo-1-(tetrahydro-2H-pyran-3-yl)-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid, 100 mg of 5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 0.42 mL of N,N-diisopropylethylamine, and 5 mL of N,N-dimethyl formamide was added 235 mg of TBTU, followed by stirring at room temperature overnight. To the reaction mixture were added water and a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0-95/5). The obtained solid was washed with methanol to obtain 148 mg of 7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-methyl-1-(tetrahydro-2H-pyran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one.

Workup

  1. extractiona saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0-95/5)
  6. washThe obtained solid was washed with methanol

Sources & evidence

ORD record
ord-b38d6939362c4b43a1eac581bcb48268
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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