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

HRID 1713090ノート

反応式

HRID 1713090 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

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 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)

出典と根拠

ORDレコード
ord-96002983f1e740629ffe38e356625425
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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