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Sodium triacetoxyborohydride → 2-(Methylamino)-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519635
ノート
印刷プレビュー

反応式

HRID 1519635 の反応式
[CH3:1][NH:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[O:19]=[C:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]=O)=[CH:28][C:23]=2[CH2:22][O:21]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][NH:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:30][CH2:29][C:27]3[CH:26]=[CH:25][C:24]4[C:20](=[O:19])[O:21][CH2:22][C:23]=4[CH:28]=3)[CH2:17][CH2:18]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]
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 5049666Sodium triacetoxyborohydrideHCID 675133682-(Methylamino)-4-(2-piperazin-1-ylethyl)benzonitrileHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

生成物 1

HCID 569708632-(Methylamino)-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒
2 回

実験手順

A solution of crude 2-(methylamino)-4-(2-piperazin-1-ylethyl)benzonitrile (˜18 mg, 0.05 mmol), (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (9 mg, 0.05 mmol) and NaBH(OAc)3 (100 mg, 0.47 mmol) in 10 mL of anhydrous DCM was stirred at ambient temperature overnight. The reaction mixture was added 50 mL of DCM and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford 2-(methylamino)-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ 7.77 (d, J=7.8, 1H), 7.22˜7.32 (m, 3H), 6.42˜6.47 (m, 2H), 5.22 (s, 2H), 4.50˜4.58 (m, 1H), 2.84˜2.91 (m, 7H), 2.72˜2.77 (m, 2H), 2.53˜2.67 (m, 10H). (0.43 μM)

後処理

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with prep-TLC

出典と根拠

ORDレコード
ord-3938c3003e1c420ab6bd635704b6ad8a
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073882B2

反応ノート

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