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

HRID 2383462노트

반응식

HRID 2383462 반응식
FC(F)(F)C([O-])=O.[CH:8]1[C:20]2[C:19]3[CH2:18][CH2:17][NH2+:16][CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1.CCN(C(C)C)C(C)C.[N:30]([C:33]1[CH:34]=[C:35]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:36]=[CH:37][C:38]=1[O:39][CH3:40])=[C:31]=[O:32].ClCCl>ClC(Cl)C.C(OCC)C>[CH3:40][O:39][C:38]1[CH:37]=[CH:36][C:35]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:34][C:33]=1[NH:30][C:31]([N:16]1[CH2:15][C:14]2[CH:13]=[N:12][C:11]3[NH:10][N:9]=[CH:8][C:20]=3[C:19]=2[CH2:18][CH2:17]1)=[O:32]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 35309923-Isocyanato-4-methoxybiphenylHCID 866455766,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

생성물 1

HCID 59490699N-(4-methoxybiphenyl-3-yl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of the 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.06 g, 0.15 mmol) and Hunig's Base (0.2 mL) in dichloroethane (2 mL) was added 3-isocyanato-4-methoxybiphenyl (0.034 g, 0.15 mmol). The mixture was stirred at room temperature for 24 hours before being poured into dichloromethane (50 mL) and washed with water (100 mL). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give an off white solid. Trituration with diethylether (20 mL) gave N-(4-methoxybiphenyl-3-yl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as an off white powder (0.030 g, 40%). M.p.=148-151° C. 1H NMR (DMSO-d6) 400 MHz δ 8.37 (s, 1H), 8.18 (s, 1H), 7.96 (s, 1H), 7.58-7.30 (m, 6H), 7.10 (d, J=8.4 Hz, 1H), 4.80 (s, 2H), 3.87-3.83 (m, 5H), 3.17 (s, 2H). LCMS [M+H]: 400.

후처리

  1. washwashed with water (100 mL)
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give an off white solid

출처 및 근거

ORD 기록
ord-73e7e98048dd49d7827df6c50eddac31
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263610B2

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