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

HRID 2223361ノート

反応式

HRID 2223361 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-44a9e0d2b5184a4e92ecfc07f334e9f8
出典データセット
uspto-grants-2008_05
特許番号
US07375131B2

反応ノート

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