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

HRID 2092968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092968
[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

Komponenten

6

Edukt 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

Produkt 1

HCID 58227559(2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanoneAusbeute 84,7 %

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-94996aa1c10849c296d338fbfeba324b
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440837B2

Notizen zur Reaktion

Wird geladen…