Dichloromethane → (2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone

HRID 2092968ノート

反応式

HRID 2092968 の反応式
[Br:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([Br:7])[N:6]=1.F[P-](F)(F)(F)(F)F.[N:18]1(OC(N(C)C)=[N+](C)C)[C:22]2C=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.N1CCCCC1.C(Cl)Cl.C(N(CC)CC)C>>[Br:1][C:2]1[S:3][C:4]([C:8]([N:18]2[CH2:24][CH2:25][CH2:26][CH2:21][CH2:22]2)=[O:10])=[C:5]([Br:7])[N:6]=1

参加物

6

反応物 5

HCID 6344DichloromethaneHCID 8082PiperidineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 151419582,4-Dibromo-1,3-thiazole-5-carboxylic acid

生成物 1

HCID 58227559(2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone収率 84.7%

実験手順

To a stirred solution of 2,4-dibromo-5-thiazole carboxylic acid (48, 400 mg, 1 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (790 mg, 2.1 mmol) and piperidine (180 uL, 1.8 mmol) in methylene chloride (5.0 mL, 78 mmol) was added triethylamine (580 μL, 4.2 mmol) at room temperature. The resulting turbid mixture was allowed to stir at rt overnight and quenched with water. The product was extracted using dichloromethane and washed with water, citric acid solution, water and brine. Removal of solvent gave the intermediate (49) (2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone (300 mg, 30%) which was used as such for the next step.

後処理

  1. customquenched with water
  2. extractionThe product was extracted
  3. washwashed with water, citric acid solution, water and brine
  4. customRemoval of solvent

出典と根拠

ORDレコード
ord-94996aa1c10849c296d338fbfeba324b
出典データセット
uspto-grants-2013_05
特許番号
US08440837B2

反応ノート

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