Sodium Iodide → 1-(4-cyclobutyl-piperazin-1-yl)-2-(7-methoxy-1,2,4,5-tetrahydro-benzo[D]azepin-3-yl)-ethanone

HRID 1713090노트

반응식

HRID 1713090 반응식
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl[CH:15]1[CH2:20][N:19]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[CH2:18][CH2:17][NH:16]1.[C:25](N)(=[O:27])[CH3:26].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH:21]1([N:19]2[CH2:18][CH2:17][N:16]([C:25](=[O:27])[CH2:26][N:9]3[CH2:10][CH2:11][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=4[CH2:7][CH2:8]3)[CH2:15][CH2:20]2)[CH2:24][CH2:23][CH2:22]1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 138533487-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepineHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

생성물 1

HCID 574206121-(4-cyclobutyl-piperazin-1-yl)-2-(7-methoxy-1,2,4,5-tetrahydro-benzo[D]azepin-3-yl)-ethanone

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 7-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (177 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 the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3). The combined extracts are dried over sodium sulfate, and the solvent is removed under reduced pressure. The resulting residue is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 6.99 (1H, d), 6.60˜6.66 (2H, m), 3.77 (3H, s), 3.60˜3.73 (4H, m), 3.26 (2H, s), 2.80˜3.00 (4H, m), 2.58˜2.73 (5H, m), 2.25˜2.40 (4H, m), 1.65˜2.10 (6H, m); MS (+VE) m/z 358.4 (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 combined extracts are dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe resulting residue is purified by PTLC (EtOAc/4% TEA)

출처 및 근거

ORD 기록
ord-96002983f1e740629ffe38e356625425
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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