Dimethylformamide → 4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-nitrophthalazin-1(2H)-one

HRID 1091727ノート

反応式

HRID 1091727 の反応式
O.[NH2:2][NH2:3].[F:4][C:5]1[CH:24]=[CH:23][C:8](/[CH:9]=[C:10]2\[O:11][C:12](=O)[C:13]3[C:18]\2=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][CH:14]=3)=[CH:7][C:6]=1[C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH3:34])[CH2:29][CH2:28]1)=[O:26].CN(C)C=O>O>[F:4][C:5]1[CH:24]=[CH:23][C:8]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[N+:19]([O-:21])=[O:20])[C:12](=[O:11])[NH:3][N:2]=2)=[CH:7][C:6]=1[C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH3:34])[CH2:29][CH2:28]1)=[O:26]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 57791796(Z)-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)-4-nitroisobenzofuran-1(3H)-one

生成物 1

HCID 577917724-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-nitrophthalazin-1(2H)-one収率 77%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Hydrazine hydrate (0.046 mL, 0.94 mmol) was added in one portion to (Z)-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)-4-nitroisobenzofuran-1(3H)-one (44) (50 mg, 0.12 mmol) and N,N-Dimethylformamide (0.045 mL, 0.59 mmol) in water (2 mL) at 25° C. under air. The resulting mixture was stirred at 100° C. for 18 hours. The mixture was cooled to ambient temperature and the solvent evaporated to give crude desired product as a pale brown solid (40.0 mg, 77% yield); 1H NMR: (400.132 MHz, DMSO) δ 1.23-1.33 (1H, m), 1.36-1.50 (1H, m), 1.65-1.72 (1H, m), 1.79-1.92 (1H, m), 3.25-3.27 (4H, m), 3.33 (3H, s), 3.82-3.97 (1H, m), 4.10 (2H, s), 7.10-7.21 (3H, m), 7.99-8.03 (1H, m), 8.27 (1H, d), 8.59 (1H, d); m/z (LC-MS, ESI+), RT=1.85 (M+H 441.3).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solvent evaporated

出典と根拠

ORDレコード
ord-44863dcc8e3c4009a9b1766931a4d9b6
出典データセット
uspto-grants-2012_03
特許番号
US08129380B2

反応ノート

読み込み中…