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N-bromobutanimide → Methyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)thiazole-5-carboxylate

HRID 252871
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252871
CO/[CH:3]=[CH:4]/[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N(Br)C(=O)C1.[C:17]([C:19]1[CH:34]=[CH:33][C:22]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30](=[S:32])[NH2:31])[CH2:26][CH2:25]2)=[CH:21][CH:20]=1)#[N:18]>O1CCOCC1.O>[C:17]([C:19]1[CH:20]=[CH:21][C:22]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]3[S:32][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][N:31]=3)[CH2:26][CH2:25]2)=[CH:33][CH:34]=1)#[N:18]
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Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 5323651Methyl 3-methoxyacrylateHCID 860404374-(4-Cyanobenzyl)piperazine-1-carbothioamide

Produkt 1

HCID 66894234Methyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)thiazole-5-carboxylateAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)
Lösungsmittel

Versuchsvorschrift

A solution of (E)-methyl 3-methoxyacrylate (290 mg, 280 mL, 2.51 mmol) in 1:1 mixture of dioxane/water (4 mL) was treated with NBS (507 mg, 2.85 mmol) at 0° C. and stirred for 1 hour. The mixture was transferred to a flask containing the thioamide 337 (593 mg, 2.28 mmol) at room temperature and the resulting mixture was refluxed for 1.5 hours. It was cooled down, quenched by adding saturated NH4Cl solution (5 mL) and concentrated. Obtained material was partitioned between EtOAc and water. Organic phase was dried with Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography using 60% EtOAc in hexanes as an eluent, to afford the title compound 338 (602 mg, 77% yield). MS: calc: 342.1; found: 343.1 (M+H)

Aufarbeitung

  1. customThe mixture was transferred to a flask
  2. temperaturethe resulting mixture was refluxed for 1.5 hours
  3. temperatureIt was cooled down
  4. customquenched
  5. additionby adding saturated NH4Cl solution (5 mL)
  6. concentrationconcentrated
  7. customObtained material was partitioned between EtOAc and water
  8. dry with materialOrganic phase was dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3db03a48cd0b4b149dd3b720fbfaac38
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868205B2

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