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

HRID 1713092노트

반응식

HRID 1713092 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

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 organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by PTLC (EtOAc/4% TEA plus 4% EtOH)

출처 및 근거

ORD 기록
ord-6f2e90cbc2974026a0b23207e1508234
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

반응 노트

불러오는 중…