Triethylamine → Dimethyl 5,5'-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate

HRID 1042937

반응식

HRID 1042937 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])=[O:9])=[CH:4][C:3]=1I.[C:30]([C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35])#[CH:31].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.[Cu]I>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])=[O:9])=[CH:4][C:3]=1[C:31]#[C:30][C:32]1[CH:38]=[CH:37][CH:36]=[C:34]([NH2:35])[CH:33]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 86668544dimethyl 5,5'-{N-[(6-amino-5-iodopridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate

생성물 1

HCID 86668543Dimethyl 5,5'-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate수율 88%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To the degassed mixture of dimethyl 5,5′-{N-[(6-amino-5-iodopridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate (1.16 g, 2.15 mmol, 1.0 equiv.), 3-ethynylaniline (0.34 mL, 3.25 mmol, 1.5 equiv.), and triethylamine (1.2 mL, 8.61 mmol, 4.0 equiv.) in anhydrous DMF (7 mL) under nitrogen atmosphere was added CuI (81.5 mg, 0.42 mmol, 0.2 equiv.) and PdCl2(Ph3P)2 (150.6 mg, 0.21 mmol, 0.1 equiv.). The reaction mixture was stirred at room temperature for 15 minutes. The reaction was then diluted with EtOAc, washed with sat. aq. NaHCO3, aq. NH4Cl, and brine, and lastly dried with anhydrous Na2SO4. The solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (from EtOAc-Hex 1:3 to neat EtOAc) to give the title compound as a white foam (1.0 g).

후처리

  1. washwashed with sat. aq. NaHCO3, aq. NH4Cl, and brine
  2. dry with materiallastly dried with anhydrous Na2SO4
  3. customThe solution was decanted
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ea7c59af467f4bc2bc2f2bdd9482a475
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08558002B2

연결된 노트

불러오는 중…