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

HRID 2383462ノート

反応式

HRID 2383462 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-73e7e98048dd49d7827df6c50eddac31
出典データセット
uspto-grants-2012_09
特許番号
US08263610B2

反応ノート

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