Water → 5-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid Amide

HRID 2223361노트

반응식

HRID 2223361 반응식
Br[C:2]1[S:6][C:5]([NH:7][C:8]([NH2:10])=[O:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=1.C(N(CC)CC)C.[C:21]1([C:27]#[CH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C.[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:21]1([C:27]#[C:28][C:2]2[S:6][C:5]([NH:7][C:8]([NH2:10])=[O:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 111846265-Bromo-2-ureidothiophene-3-carboxamide

생성물 1

HCID 100167795-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid Amide수율 18%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

5-Bromo-2-ureido-thiophene-3-carboxylic acid amide (0.264 g, 1.0 mmol), copper (I) iodide (0.005 g), triphenyl phosphene (0.030 g, 15 mole %), palladium acetate (0.010 g, 5% mole %), triethyl amine (1 mL) and phenylacetylene (0.1 g, 1.1 mmol) in DMF (4 mL) was added to a 9 mL reaction vial. The reaction vial was sealed and heated to 100° C. in a Smith Microwave Synthesizer for 20 min. Water (5 mL) and ethyl acetate (20 mL) were added to the reaction mixture, the organic phase was separated and then washed with brine (2×10 mL) and water (1×10 mL), and dried over anhydrous magneium sulfate. After filtration, the solvent was removed under vacuum and the crude residue was taken into DMSO (5 mL) and purified utilizing a Gilson preparative HPLC to give the above titled compound as a light brown solid (0.050 g, 0.18 mmol, 18% yield). LC-MS [M+H]+ m/z 286.

후처리

  1. customThe reaction
  2. customvial was sealed
  3. customthe organic phase was separated
  4. washwashed with brine (2×10 mL) and water (1×10 mL)
  5. dry with materialdried over anhydrous magneium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum
  8. custompurified

출처 및 근거

ORD 기록
ord-44a9e0d2b5184a4e92ecfc07f334e9f8
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375131B2

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