Diisopropylethylamine → HCID 56928710, compound

HRID 1396676Notes

Reaction equation

HRID 1396676 reaction equation
[F: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][O:18][CH2:17][CH2:16]2)=[N:13][CH:14]=3)=[CH:4][C:3]=1[C:22]([OH:24])=O.[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.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F: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][O:18][CH2:17][CH2:16]2)=[N:13][CH:14]=3)=[CH:4][C:3]=1[C:22]([N:33]1[C:30]2=[CH:31][N:32]=[C:27]([O:26][CH3:25])[CH:28]=[C:29]2[CH2:35][CH2:34]1)=[O:24]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 234340355-Methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridineHCID 68018999HCID 68018999, compound

Product 1

HCID 56928710HCID 56928710, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 106 mg of 8-fluoro-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid, 53 mg of 5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 0.22 mL of N,N-diisopropylethylamine, and 2 mL of N,N-dimethyl formamide was added 146 mg of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, followed by stirring at room temperature overnight. To the reaction mixture was added 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 preparative HPLC (methanol/0.1% aqueous formic acid solution) to obtain 5.9 mg of 8-fluoro-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-1-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]quinoxalin-4(5H)-one as a pale brown solid.

Workup

  1. extractionfollowed 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 preparative HPLC (methanol/0.1% aqueous formic acid solution)

Sources & evidence

ORD record
ord-b5ffbd9342464375a22885f4e9fc1e00
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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