Triethylamine → dimethyl 5,5'-[N-({6-amino-5-[(4-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate

HRID 1042941노트

반응식

HRID 1042941 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:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)#[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][C:35]([NH2:36])=[CH:34][CH:33]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 37600254-EthynylanilineHCID 86668544dimethyl 5,5'-{N-[(6-amino-5-iodopridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate

생성물 1

HCID 86668546dimethyl 5,5'-[N-({6-amino-5-[(4-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate수율 95.9%

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-iodopyridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate (234 mg, 0.434 mmol, 1.0 equiv.), 4-ethynylaniline (76.3 mg, 0.651 mmol, 1.5 equiv.), and triethylamine (0.242 mL, 1.736 mmol, 4.0 equiv.) in anhydrous DMF (2 mL) under nitrogen atmosphere was added CuI (16.5 mg, 0.087 mmol, 0.2 equiv.) and PdCl2(Ph3P)2 (30.5 mg, 0.043 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 EtOAc) yielding dimethyl 5,5′-[N-({6-amino-5-[(4-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate as brown oil (220 mg).

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-d0347535fe854422b39a96941067f802
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08558002B2

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