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

HRID 1713078노트

반응식

HRID 1713078 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3670cd2a4f1f4a39bd2af8de7783d979
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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