Ethyl Acetate → N-[2-Methoxy-4-(6-([(1S)-1-pyridin-3-ylbutyl]amino)pyrazin-2-yl)phenyl]-N'-ethylurea

HRID 1943776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943776
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH3:12])[CH:5]=[N:4][CH:3]=1.[C:19](=[O:22])([O-])[O-].[Na+].[Na+].[C:25]([O:28][CH2:29][CH3:30])(=O)C>C(O)CC.C1(C)C=CC=CC=1.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>[CH3:25][O:28][C:29]1[CH:30]=[C:12]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C@H:9]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH2:10][CH2:11][CH3:12])[N:7]=2)[CH:11]=[CH:10][C:9]=1[NH:8][C:19]([NH:4][CH2:3][CH3:2])=[O:22]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 597773706-chloro-N-[(1S)-1-pyridin-3-ylbutyl]pyrazin-2-amine

Produkt 1

HCID 11235499N-[2-Methoxy-4-(6-([(1S)-1-pyridin-3-ylbutyl]amino)pyrazin-2-yl)phenyl]-N'-ethylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 22495535HCID 22495535, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under a nitrogen atmosphere a mixture of 6-chloro-N-[(1S)-1-pyridin-3-ylbutyl]pyrazin-2-amine (53 g, 0.2 mmol), 4-{[(ethylamino)carbonyl]amino}-3-methoxyphenylboronic acid pinacol diester (69 mg, 0.23 mmol), tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol) in toluene—n-propanol (2.6 mL, 3:1) was treated with 2M aqueous sodium carbonate solution (0.15 mL, 0.3 mmol). The resulting mixture was stirred vigorously whilst being heated at 100° C. for 22 hours. Once cool ethyl acetate (10 mL) was added and the mixture washed with H2O (6×10 mL) and brine (10 mL) and then dried (Na2SO4). Removal of solvent in vacuo then yielded crude product, which was purified by column chromatography using dichloromethane-methanol-aqueous ammonia (93:7:1) as eluent to furnish the product (60 mg).

Aufarbeitung

  1. washthe mixture washed with H2O (6×10 mL) and brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of solvent in vacuo
  4. customthen yielded crude product, which
  5. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-61ed18b28b0b497d87c4cdbac9e096e8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394806B2

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