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Hydrazine → N-cyclopentyl-4-[2-(4-fluorophenyl)-7-hydrazinopyrazolo[1,5-a]pyridin-3-yl]-6-methyl-2-pyrimidinamine

HRID 1373795
ノート
印刷プレビュー

反応式

HRID 1373795 の反応式
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:10]([C:11]3[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH2:31][NH2:32]>C(O)C.C(OCC)(=O)C>[CH:19]1([NH:18][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[N:8][N:7]4[C:2]([NH:31][NH2:32])=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[C:15]([CH3:17])[N:14]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 9321HydrazineHCID 102957644-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-6-methyl-2-pyrimidinamine

生成物 1

HCID 10202082N-cyclopentyl-4-[2-(4-fluorophenyl)-7-hydrazinopyrazolo[1,5-a]pyridin-3-yl]-6-methyl-2-pyrimidinamine収率 46%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate
溶媒

反応条件

温度
90 °C

実験手順

To a solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-methyl-2-pyrimidinamine (100 mg, 0.237 mmol) in ethanol (1 mL) was added hydrazine (500 uL, 15.9 mmol). The reaction mixture was heated in a sealed tube at 90° C. for 72 hours. The mixture was cooled and diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water and brine. The combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (38:2 dichloromethane-methanol) provided N-cyclopentyl-4-[2-(4-fluorophenyl)-7-hydrazinopyrazolo[1,5-α]pyridin-3-yl]-6-methyl-2-pyrimidinamine (45 mg, 46%) as a yellow solid. Rf 0.43 (38:2 CH2Cl2-MeOH); 1H NMR (CDCl3) δ 7.78 (1H), 7.62 (2H), 7.35 (1H), 7.20 (1H), 7.12 (2H), 6.45 (1H), 6.24 (1H), 5.03 (1H), 4.35 (1H), 3.85 (2H), 2.18 (3H), 2.02 (2H), 1.62 (6H); MS m/z 418 (M+1).

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with saturated aqueous sodium bicarbonate, water and brine
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-3973ba1c19b24b729ead74990c190b1c
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07163940B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート