Phenyl isocyanate → N-phenyl-1-o-tolyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

HRID 2383486Notes

Reaction equation

HRID 2383486 reaction equation
Cl.[C:2]1([CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[CH2:18][CH2:17][NH:16][CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1.C(N(CC)CC)C.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[C:29]1([NH:35][C:36]([N:16]2[CH2:15][C:14]3[CH:13]=[N:12][C:11]4[NH:10][N:9]=[C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[CH3:21])[C:20]=4[C:19]=3[CH2:18][CH2:17]2)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 178424205HCID 178424205, compound

Product 1

HCID 178424206N-phenyl-1-o-tolyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the crude 1-o-tolyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine hydrochloride salt obtained from step 2 was added anhydrous tetrahydrofuran (1.5 mL) and triethylamine (50 μL) followed by 400 mM solution of phenyl isocyanate (0.25 mL) in tetrahydrofuran. The reaction mixture was shaken at room temperature for 6 hours. The solvent was then removed under reduced pressure and the crude product was purified using reverse phase HPLC to give the pure desired product, N-phenyl-1-o-tolyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide. LCMS [M+H]: 384.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-27b0efb1f9cc475285e224cb3456d46f
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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