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1,4-Dioxane → 1-Benzothiazol-6-yl-3-(4-pyrrolidin-1-ylmethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80235
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HRID 80235 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.CNC1C[CH2:22][CH2:21][CH2:20][CH:19]1[NH:24][CH3:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:39][CH2:38]OCC1>C(Cl)Cl.[Cu](I)I.CO>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:5]4[CH:4]=[N:3][CH:2]=[CH:38][C:39]=4[CH2:25][N:24]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1
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참가 물질

8

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

생성물 1

HCID 498726511-Benzothiazol-6-yl-3-(4-pyrrolidin-1-ylmethyl-pyridin-3-yl)-imidazolidin-2-one수율 18.9%

시약·촉매·용매 3

HCID 83717
Copper iodide
촉매
HCID 887Methanol용매
HCID 6344Dichloromethane용매

실험 절차

Using the same reaction conditions and work up as described in Example 1, step -3,3-bromo-4-pyrrolidin-1-ylmethyl-pyridine (I-176a: 290 mg, 1.205 mmol) was refluxed with 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 220 mg, 1.004 mmol), copper iodide (19 mg, 0.1004 mmol), N,N′-Dimethyl-cyclohexane-1,2-diamine (42.7 mg, 0.301 mmol), potassium phosphate (640 mg, 3.012 mmol) and 1,4-dioxane (15 mL) at 120° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (5% MeOH in DCM). Purification by column chromatography on silica gel (5% MeOH in chloroform) followed by preparative HPLC afforded 72 mg of the product (18.9% yield).

후처리

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (5% MeOH in chloroform)

출처 및 근거

ORD 기록
ord-3096c593b7704a7dbfc86954866657e1
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE045173E1

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