Sodium Iodide → 2-[2-(4-Cyclobutyl-piperazin-1-yl)-2-oxo-ethyl]-1,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methylamide

HRID 1713092ノート

反応式

HRID 1713092 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].Cl[CH:16]1[CH2:21][N:20]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[CH2:19][CH2:18][NH:17]1.[C:26](N)(=[O:28])[CH3:27].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH3:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([CH2:27][C:26]([N:17]3[CH2:18][CH2:19][N:20]([CH:22]4[CH2:25][CH2:24][CH2:23]4)[CH2:21][CH2:16]3)=[O:28])[CH2:12]2)=[CH:7][CH:6]=1)=[O:4]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 57479413N-methyl-1,2,3,4-tetrahydroisoquinoline-7-carboxamideHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

生成物 1

HCID 594635382-[2-(4-Cyclobutyl-piperazin-1-yl)-2-oxo-ethyl]-1,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methylamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 1,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methylamide (96 mg, 0.5 mmol) in acetonitrile (3.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (109 mg, 0.5 mmol, 1.0 eq.), K2CO3 (138 mg, 1.0 mmol, 2.0 eq.), and NaI (10 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), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by PTLC (EtOAc/4% TEA plus 4% EtOH) to give the title compound. MS (+VE) m/z 371.1 (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 organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by PTLC (EtOAc/4% TEA plus 4% EtOH)

出典と根拠

ORDレコード
ord-6f2e90cbc2974026a0b23207e1508234
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…