N-Hydroxyacetamidine → N-ethanimidoyl-3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzamide

HRID 216144

Reaktionsgleichung

Reaktionsgleichung von HRID 216144
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH:6]=[C:5]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:4]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:60](=[N:63]O)([NH2:62])[CH3:61]>CN(C)C=O.O>[NH:62]=[C:60]([NH:63][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([C:7]2[CH:6]=[C:5]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:4]=[C:3]([O:2][CH3:1])[N:8]=2)[CH:10]=1)[CH3:61]

Komponenten

7

Edukt 4

HCID 30926N-HydroxyacetamidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 116033013-{2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Produkt 1

HCID 148920926N-ethanimidoyl-3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid (200 mg, 0.53 mmol, Example 35(a)] in dimethylformamide (1.75 mL) is added diisopropylethylamine (0.23 mL, 1.33 mmol) followed by TBTU (205 mg, 0.64 mmol). Stirred the solution for 15 minutes before adding acetamide oxime (59 mg, 0.8 mmol). After 4 hours of stirring at ambient temperature the mixture is diluted with water (20 mL) and extracted twice with EtOAc (20 mL). The combined organic extracts are washed three times with water (20 mL), with brine (20 mL), dried over magnesium sulfate, filtered and concentrated by rotary evaporator to provide N-(1-imino-ethyl)-3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide [60 mg, 69%, Intermediate (45)].

Aufarbeitung

  1. stirringAfter 4 hours of stirring at ambient temperature the mixture
  2. extractionextracted twice with EtOAc (20 mL)
  3. washThe combined organic extracts are washed three times with water (20 mL)
  4. dry with materialwith brine (20 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-7f62c8cd99364990a4f394b63ea95e98
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193183B2

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