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4-Methylmorpholine → 4-[7-Bromo-2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1963098
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1963098
[Br:1][C:2]1[CH:3]=[CH:4][N:5]2[C:9]([CH:10]=1)=[C:8]([C:11]([OH:13])=O)[C:7]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH3:22])=[C:6]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:11]([C:8]2[C:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=3[CH3:22])=[C:6]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:5]3[C:9]=2[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4]3)=[O:13])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:30])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 677729597-Bromo-2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid

Produkt 1

HCID 67772864
4-[7-Bromo-2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester
Ausbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the crude compound obtained in step 2 (219 mg, 0.50 mmol), 1-tert-butoxycarbonyl-piperazine (98 mg, 0.55 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (105 mg, 0.55 mmol) and 1-hydroxybenzotriazole (88 mg, 0.58 mmol) in DMF (5 ml) was added N-methyl-morpholine (330 μl, 3.00 mmol), and the mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (HEP/EA). 300 mg of the title compound were obtained.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (HEP/EA)

Quellen und Nachweise

ORD-Eintrag
ord-3719fa88d7c14b50beea0ef71aec614b
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415336B2

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