Aniline → N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

HRID 2383464Notes

Reaction equation

HRID 2383464 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:21](Cl)=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:27]1([NH:26][C:21]([N:17]2[CH2:16][C:15]3[CH:14]=[N:13][C:12]4[NH:8][N:9]=[CH:10][C:11]=4[C:20]=3[CH2:19][CH2:18]2)=[O:22])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:21]([NH:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 594905863-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carbonyl chloride

Product 2

HCID 46836849N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamideHCID 594905663-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Step (i): To a 0.1M solution of 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carbonyl chloride (0.5 mL, 0.050 mmol) in anhydrous DMF was added a 0.1M solution of aniline (0.75 mL, 0.075 mmol) in anhydrous DMF. The reaction mixture allowed shaken at 80° C. for 16 hours. The solvent was removed under reduced pressure and to give the desired product, 3-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a solid, which was used in the next step without any further purification. Step (ii): To the product obtained in Step 2(i) was added trifluoroacetic acid (1 mL). The reaction mixture was heated at 70° C. for 16 hours. On the completion of the reaction, toluene (3 mL) was added and the solvent removed under reduced pressure. The crude product was purified using reverse phase HPLC to give the desired product, N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a white solid. LCMS [M+H]: 294.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d480944532d34890a3bca74ec0536772
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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