Sodium Iodide → 1-(4-cyclobutyl-piperazin-1-yl)-2-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone

HRID 1713078ノート

反応式

HRID 1713078 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.Cl[CH:14]1[CH2:19][N:18]([CH:20]2[CH2:23][CH2:22][CH2:21]2)[CH2:17][CH2:16][NH:15]1.[C:24](N)(=[O:26])[CH3:25].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH:20]1([N:18]2[CH2:17][CH2:16][N:15]([C:24](=[O:26])[CH2:25][N:8]3[CH2:7][CH2:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:9]3)[CH2:14][CH2:19]2)[CH2:23][CH2:22][CH2:21]1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

生成物 1

HCID 247512261-(4-cyclobutyl-piperazin-1-yl)-2-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (163 mg, 1.0 mmol) in acetonitrile (5.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (216 mg, 1.0 mmol, 1.0 eq.), K2CO3 (376 mg, 2.0 mmol, 2.0 eq.), and NaI (30 mg). The resulting mixture is stirred at rt overnight. Water (10.0 ml) is added to quench the reaction, and then the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3). The extracts are dried over sodium sulfate, and the solvent is removed under reduced pressure to yield a residue that is purified through PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 6.92 (1H, d), 6.70 (1H, dd), 6.63 (1H, d), 3.77 (3H, s), 3.58˜3.68 (6H, m), 3.33 (2H, s), 2.86 (2H, t), 2.74 (2H, t), 2.65 (1H, m), 2.27 (4H, m), 1.62˜2.06 (6H, m); MS (+VE) m/z 344.2 (M++1).

後処理

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (10 ml×3)
  5. dry with materialThe extracts are dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customto yield a residue that
  8. customis purified through PTLC (EtOAc/4% TEA)

出典と根拠

ORDレコード
ord-3670cd2a4f1f4a39bd2af8de7783d979
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

読み込み中…