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Hydrochloric Acid → 2-[4-(benzyloxy)phenyl]-N-[3-bromo-1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide

HRID 1790161
ノート
印刷プレビュー

反応式

HRID 1790161 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][N:23]3[CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Br-:37].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>O.CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[C:21]([Br:37])=[N:22][N:23]3[CH2:28][CH2:29][N:30]2[CH2:31][CH2:32][CH2:33][CH2:34]2)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 114196662-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamideHCID 21124087Pyridiniumtribromide

生成物 1

HCID 117207372-[4-(benzyloxy)phenyl]-N-[3-bromo-1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
2 回
HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide (Example 3, 0.200 g, 0.440 mmol) and NaOH (0.400 g, 10.0 mmol) in H2O (6 mL) was added in methanol (6 mL) was placed in an ice-water bath for 15 minutes before pyridinium tribromide (0.470 g, 1.47 mmol) in MeOH (1.5 mL) was added. The reaction mixture was stirred at 0° C. for 5 hours after which the pH was adjusted to 7 with diluted HCl. The mixture was extracted with ethyl acetate, and the combined organic layer washed with H2O and concentrated under reduced pressure. The residue was purified by flash chromatography to provide the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 1.60 (m, 4H), 2.43 (m, 4H), 2.85 (t, 2H, J=6.44), 3.68 (s, 2H), 4.48 (t, 2H, J=6.44), 5.10 (s, 2H), 7.00 (d, 2H, J=8.47), 7.29–7.48 (m, 7H), 7.55 (s, 2H), 7.64 (s, 1H), 10.05 (s, 1H); MS (DCI/NH3) m/z 533 [M+H]+.

後処理

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic layer washed with H2O
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-c6bb2a64285e402fb31d762dc9f96674
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07071182B2

反応ノート

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