1,4-Dioxane → 1-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

HRID 132606

반응식

HRID 132606 반응식
[NH2:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[Cu][C:22]#[N:23].[O:24]1[CH2:29]COCC1>[C-]#N.C([N+](CC)(CC)CC)C.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:3]1[C:2]([NH:1][C:29]([NH:23][C:22]2[CH:14]=[CH:13][C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:16]=2)=[O:24])=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)([CH3:20])([CH3:19])[CH3:18]

참가 물질

8

반응물 3

HCID 312751,4-DioxaneHCID 685300435-Amino-6-(2-tert-butylphenoxy)nicotinonitrileHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 115540381-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

시약·촉매·용매 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 3014735Tetraethylammonium cyanide촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 3283Diethyl Ether용매

반응 조건

온도
105 °C

실험 절차

5-Amino-6-(2-tert-butylphenoxy)nicotinonitrile: A mixture of 63c (676 mg, 2.1 mmol), copper (1) cyanide (755 mg, 8.4 mmol), tris(dibenzilideneacetone)dipalladium(0) (77 mg, 0.08 mmol), bis(diphenylphosphino)ferrocene (187 mg, 0.34 mmol) and tetraethylammonium cyanide (330 mg, 2.1 mmol) in dioxane (11 mL) was heated at 105° C. overnight. The mixture was cooled to rt, diluted with ether (50 mL), filtered through Celite® and silica (3 g) and concentrated to give a brown solid (883 mg). The solid was purified by SiO2 chromatography (40 g) to afford 63d (472 mg. 84% yield) as a yellow solid; HPLC purity 95%, 3.37 min (Method A); [M+H]+=268.15; 1H NMR (CDCl3) δ ppm: 1.35 (s, 9 H) 4.26 (s, 2 H) 6.95 (d, J=7.70 Hz, 1 H) 7.15 (s, 1 H) 7.20 (t, J=7.70 Hz, 1 H) 7.25 (t, J=7.42 Hz, 1 H) 7.47 (d, J=7.70 Hz, 1 H) 7.82 (s, 1 H); 13C NMR (CDCl3) δ ppm: 154.22, 151.27, 141.40, 139.75, 131.98, 127.57, 127.03, 125.53, 123.53, 121.69, 117.38, 104.08, 34.60, 30.47.

후처리

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite® and silica (3 g)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-901db812d251499d9e832bd475385333
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388021B2

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