Potassium Phosphate, Tribasic → 1-Benzothiazol-6-yl-4-methyl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80220

반응식

HRID 80220 반응식
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH:13]([CH3:15])[NH:12][C:11]3=[O:16])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].CNC1CCCCC1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH:13]([CH3:15])[N:12]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][C:23]=4[CH3:24])[C:11]3=[O:16])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 144235133-Iodo-4-methylpyridineHCID 596362111-Benzothiazol-6-yl-4-methyl-imidazolidin-2-one

생성물 1

HCID 498719611-Benzothiazol-6-yl-4-methyl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one수율 16.66%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 887Methanol용매HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

실험 절차

Using the same reaction conditions and work up as described in Example 1, step-3,1-benzothiazol-6-yl-4-methyl-imidazolidin-2-one (I-167b: 150 mg, 0.643 mmol) was refluxed with 3-iodo-4-methyl-pyridine (155 mg, 0.708 mmol), copper iodide (12.21 mg, 0.0643 mmol), N,N′-dimethyl-cyclohexane-1,2-diamine (27.39 mg, 0.192 mmol), potassium phosphate (341.5 mg, 1.607 mmol) and 1,4-dioxane (5 mL) at 120° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (10% MeOH in chloroform). Purification by column chromatography on silica gel (3% methanol in chloroform) followed by preparative HPLC afforded 34 mg of the product (16.66% yield).

후처리

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

출처 및 근거

ORD 기록
ord-c7f55d5db3414a5da3720921e0304c55
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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