Ammonium formate → N-cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclobutylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide

HRID 2070782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070782
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH:19][C:20]2[C:21](=[O:40])[N:22]([C:27]3[CH:28]=[C:29]([CH:36]=[CH:37][C:38]=3[CH3:39])[C:30]([NH:32][CH:33]3[CH2:35][CH2:34]3)=[O:31])[CH:23]=[C:24](Br)[N:25]=2)[CH2:18][CH2:17][CH2:16]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH:33]1([NH:32][C:30](=[O:31])[C:29]2[CH:36]=[CH:37][C:38]([CH3:39])=[C:27]([N:22]3[CH:23]=[CH:24][N:25]=[C:20]([NH:19][C:15]4([C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[OH:8])[CH2:18][CH2:17][CH2:16]4)[C:21]3=[O:40])[CH:28]=2)[CH2:34][CH2:35]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 666896093-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 66688790N-cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclobutylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamideAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-4-methylbenzamide (Example 268e, 1.537 g) in ethanol (16 mL) was added ammonium formate (2.263 g) and 5% Pd/C (0.546 g) and the reaction heated at 75° C. for 1 h. The mixture was filtered through celite and the solid washed through with ethanol and dichloromethane. The filtrate was collected and the volatiles removed in vacuo. The residue was purified (SiO2 chromatography eluting with 0-30% diethyl ether in dichloromethane) to afford the subtitle product (0.874 g).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. washthe solid washed through with ethanol and dichloromethane
  3. customThe filtrate was collected
  4. customthe volatiles removed in vacuo
  5. customThe residue was purified
  6. wash(SiO2 chromatography eluting with 0-30% diethyl ether in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-7563818d58a24c618b711e6860e16577
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299246B2

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