Triethylamine → 4-[(3-Aminoisoquinolin-1-yl)ethynyl]benzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

HRID 583712

반응식

HRID 583712 반응식
[CH2:1]([O:3][C:4](=[O:28])[C@@H:5]([NH:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[CH:16])=[CH:11][CH:10]=1)[CH3:2].[NH2:29][C:30]1[N:31]=[C:32](Br)[C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2.C(N(CC)CC)C>C(#N)C.CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:28])[C@@H:5]([NH:18][S:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:20])=[O:21])[CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:10]=[CH:11][C:12]([C:15]#[C:16][C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:39]=[C:30]([NH2:29])[N:31]=2)=[CH:13][CH:14]=1)[CH3:2]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 2898451-Bromoisoquinolin-3-amineHCID 867524584-Ethynylbenzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

생성물 1

HCID 867543454-[(3-Aminoisoquinolin-1-yl)ethynyl]benzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Ethyl ester 35-3 (0.50 g, 1.25 mmol), 3-amino-1-bromoisoquinoline (0.279 g, 1.25 mmol), triethylamine (0.697 mL, 5.00 mmol), CuI (10 mg, 0.053 mmol), and (Ph3P)2PdCl2 (20 mg, 0.028 mmol) were combined in 5 mL acetonitrile in a sealed pressure tube under Ar and heated to 100° C. overnight. The dark solution was cooled and diluted with EtOAc, then washed with water (2×) and brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (silica, 75% EtOAc/Hexane) gave 35-4 as a greenish foam.

후처리

  1. temperatureThe dark solution was cooled
  2. washwashed with water (2×) and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6898179a3d1c4f5ea3eb85a2fc633743
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929120

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