Hydrochloric Acid → 1-Ethyl-3-(3-phenylethynylpyrido[2,3-b]pyrazin-6-yl)urea

HRID 1511818노트

반응식

HRID 1511818 반응식
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.C(N(CC)CC)C.[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C)C=O.ClCCl.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:16]([NH:15][C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:5]2[C:6]([N:8]=1)=[N:7][C:2]([C:32]#[C:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:3][N:4]=2)=[O:14])[CH3:17]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 588817911-(3-Chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea

생성물 1

HCID 166665761-Ethyl-3-(3-phenylethynylpyrido[2,3-b]pyrazin-6-yl)urea

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

98.1 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.39 mmol), 10.1 mg copper(I) iodide (0.05 mmol) and 193 μl of triethylamine (1.38 mmol) were initially charged in 2 ml of anhydrous dimethylformamide under nitrogen as a protective gas. Subsequently, 29.1 mg of dichlorobis(triphenylphosphine)palladium(II) (0.04 mmol) and 54 μl of phenylacetylene (0.49 mmol) were added, and the mixture was stirred at room temperature for 16 h. For workup, the mixture was diluted with dichloromethane and added to dilute hydrochloric acid. The precipitated solid was filtered off with suction, and the organic phase was washed with dilute hydrochloric acid and distilled water. After phase separation, the organic solvent was removed under reduced pressure. The further purification was effected by column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid.

후처리

  1. filtrationThe precipitated solid was filtered off with suction
  2. washthe organic phase was washed with dilute hydrochloric acid
  3. distillationdistilled water
  4. customAfter phase separation
  5. customthe organic solvent was removed under reduced pressure
  6. customThe further purification
  7. customThis gave a yellow solid

출처 및 근거

ORD 기록
ord-fc021ba4f70941f59ebcc2a51c1df7dd
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217042B2

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