Biphenyl → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-(1-propyl-1H-imidazol-2-yl)pyrazin-2-amine

HRID 1824231노트

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HRID 1824231 반응식
Br[C:2]1[C:7]([CH2:8][CH3:9])=[N:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:4]([CH2:18][CH3:19])[N:3]=1.[CH2:20]([N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28])[CH2:21][CH3:22].C1(C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1.C([O-])(O)=O.[Na+].[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:5]1[N:6]=[C:7]([CH2:8][CH3:9])[C:2]([NH:28][C:24]2[N:23]([CH2:20][CH2:21][CH3:22])[CH:27]=[CH:26][N:25]=2)=[N:3][C:4]=1[CH2:18][CH3:19]

참가 물질

8

반응물 4

HCID 7095BiphenylHCID 221474372-Bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazineHCID 221475261-propyl-1H-imidazol-2-amineHCID 23676156Sodium t-butoxide

생성물 1

HCID 103097425-(2,4-dichlorophenyl)-3,6-diethyl-N-(1-propyl-1H-imidazol-2-yl)pyrazin-2-amine수율 27.2%

시약·촉매·용매 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 312751,4-Dioxane용매HCID 516892Sodium Bicarbonate용매

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온도
110 °C

실험 절차

A mixture of 2-bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine (0.25 g, 0.69 mmol), 1-propyl-1H-imidazol-2-amine (0.15 g, 1.2 mmol), tris(dibenzylideneacetone) dipalladium (0.032 g, 0.032 mmol), 2-dicyclohexylphosphino)biphenyl (0.037 g, 0.12 mmol), and sodium tert-butoxide (0.093 g, 0.97 mmol) in dioxane (2.0 mL) was heated at 110° C. for 21 h. After cooling to rt, the reaction was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with (Biotage, 40S) with heptanes/EtOAc (3:1) to give 0.076 g (27%) of dark yellow oil: 1H NMR (400 MHz, CDCl3) δ 12.86, 7.47, 7.31, 6.70, 6.55, 3.94, 2.97, 2.48, 2.97, 2.48, 1.84, 1.30, 1.21, 0.98; IR (liq.) 2968, 2934, 1599, 1556, 1549, 1509, 1460, 1422, 1402, 1384, 1373, 1302, 1174, 1102, 712 cm1; HRMS (FAB) calcd for C20H23Cl2N5+H 404.1408, found 404.1416.

후처리

  1. temperatureAfter cooling to rt
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (Biotage, 40M) with (Biotage, 40S) with heptanes/EtOAc (3:1)

출처 및 근거

ORD 기록
ord-8daea14932354072bcc5576a76fdd17d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041672B2

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