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

HRID 1511818ノート

反応式

HRID 1511818 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc021ba4f70941f59ebcc2a51c1df7dd
出典データセット
uspto-grants-2012_07
特許番号
US08217042B2

反応ノート

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