1,2-Diaminocyclohexane, trans- → 1-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one

HRID 80111

반응식

HRID 80111 반응식
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[Cl:23].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:22]=4[Cl:23])[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 8176963-Bromo-4-chloropyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

생성물 1

HCID 596362211-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one수율 37.7%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 312751,4-Dioxane용매

실험 절차

Using the same reaction conditions as in Example 14, 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 0.150 g, 0.684 mmol) was reacted with 3-bromo-4-chloro-pyridine (0.157 g, 0.820 mmol), 1,4-dioxane (20 mL), copper iodide (0.012 g, 0.0684 mmol), trans-1,2-diamino cyclohexane (0.022 g. 0.20 mmol) and potassium phosphate (0.362 g, 1.71 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 85 mg of the product (37.7% yield).

후처리

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-c6448583e65d41efb638aa00cd6f3104
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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