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

HRID 2383464
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HRID 2383464 반응식
[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
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참가 물질

5

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  1. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-d480944532d34890a3bca74ec0536772
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263610B2

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