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Dimethylformamide → N-(1-Cyanoisoquinolin-5-yl)-N'-[4(trifluoromethyl)benzyl]urea

HRID 1181494
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1181494
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:27][N:28](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1)#[N:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 99997771-(1-Chloro-isoquinolin-5-yl)-3-(4-trifluoromethyl-benzyl)-urea

Produkt 1

HCID 69522104N-(1-Cyanoisoquinolin-5-yl)-N'-[4(trifluoromethyl)benzyl]ureaAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator
2×

Versuchsvorschrift

To a solution of N-(1-chloroisoquinolin-5-yl)-N′-[4-(trifluoromethyl)benzyl]urea (Example 69) (250 mg, 0.7 mmol) in DMF (5 ml) was added zinc cyanide (43 mg, 0.37 mmol) and tetrakis(triphenylphosphine)palladium (76 mg, 0.07 mmol). The reaction was heated at 80° C., under an atmosphere of nitrogen, for 72 hr, with the addition of extra tetrakis(triphenylphosphine)palladium (76 mg, 0.07 mmol) after 16 hr. Reaction mixture was quenched with water and extracted with ethyl acetate (3×5 ml), dried over MgSO4 and evaporated. The residue was purified by flash column chromatography using an eluant system of 3% methanol/97% DCM increasing to 5% MeOH/95% DCM. Recrystallisation in ethanol of a small portion of product gave a pure sample of the title compound (50 mg, 65.6%). m/z (ES+) 371, 373 (M+H)+.

Aufarbeitung

  1. customReaction mixture
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate (3×5 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography
  7. customRecrystallisation in ethanol of a small portion of product

Quellen und Nachweise

ORD-Eintrag
ord-c88852c606a94588ae1f91b7de276238
Quelldatensatz
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07285563B2

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