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2-(Dimethylamino)acetohydrazide → (2R)-N-[3-(5-{5-[(Dimethylamino)Methyl](1H-1,2,4-Triazol-3-Yl)}(1H-Indazol-3-Yl))Phenyl]-2-Hydroxy-2-Phenylacetamide

HRID 1349836
ノート
印刷プレビュー

反応式

HRID 1349836 の反応式
Cl.C(O[N:5]=[CH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:32])[C@H:24]([OH:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=1)C.[NH2:33][NH:34][C:35](=O)[CH2:36][N:37]([CH3:39])[CH3:38].C[O-].[Na+]>CO>[CH3:38][N:37]([CH2:36][C:35]1[NH:34][N:33]=[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:32])[C@H:24]([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:19]=[CH:20][CH:21]=2)[N:5]=1)[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 86585601(2R)-N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-2-hydroxy-2-phenylacetamide hydrochloride

生成物 1

HCID 20788990(2R)-N-[3-(5-{5-[(Dimethylamino)Methyl](1H-1,2,4-Triazol-3-Yl)}(1H-Indazol-3-Yl))Phenyl]-2-Hydroxy-2-Phenylacetamide収率 9%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒
2 回

実験手順

To a suspension of (2R)-N-{3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl}-2-hydroxy-2-phenylacetamide hydrochloride (0.500 g, 1.11 mmol) in methanol (10 mL) were added 3 equivalents of N-amino-2-(dimethylamino)acetamide (0.390 g, 3.33 mmol) and 2.5 equivalents of sodium methoxide in methanol (0.635 mL, 4.3 M). After stirring at room temperature for 1 h, the reaction mixture was heated to 95° C. for 48 hours. The reaction was then quenched with water, the pH adjusted to neutral and the crude product extracted with ethyl acetate. The title compound was purified by preparative HPLC (0.050 g, 9% yield): 1H NMR (CD3OD) δ 8.72 (s, 1H), 8.23 (s, 1H), 8.08 (d, 1H), 7.89 (d, 2H), 7.68 (d, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.40–7.32 (m, 3H), 5.21 (s, 1H), 3.71 (s, 2H), 2.37 (s, 6H); ES-MS (m/z) 468 [M+H]+.

後処理

  1. temperaturethe reaction mixture was heated to 95° C. for 48 hours
  2. customThe reaction was then quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe title compound was purified by preparative HPLC (0.050 g, 9% yield)

出典と根拠

ORDレコード
ord-2225a4a8a623484bbbad9725cbf30e39
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07211594B2

反応ノート

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