Acetic Acid → 1-[4-[4-Amino-5-(2-methoxybenzoyl)pyrimidin-2-ylamino]-piperidin-1-yl]ethanone

HRID 1435179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435179
F[C:2](F)(F)[C:3]([OH:5])=O.[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[O:16])=[CH:13][N:12]=[C:11]([NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[N:10]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(O)(=O)C>CN(C)C=O.C(OCC)(=O)C>[NH2:8][C:9]1[C:14]([C:15](=[O:16])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:13][N:12]=[C:11]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:3](=[O:5])[CH3:2])[CH2:28][CH2:27]2)[N:10]=1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69014044[4-Amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(2-methoxy-phenyl)-methanone trifluoroacetic acid salt

Produkt 1

HCID 99991551-[4-[4-Amino-5-(2-methoxybenzoyl)pyrimidin-2-ylamino]-piperidin-1-yl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(2-methoxy-phenyl)-methanone trifluoroacetic acid salt, (31 mg, Example 11) in dimethylformamide (2 mL) were added triethylamine (19 mg, 0.193 mmol, Aldrich), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.6 mg, 0.0344 mmol, Aldrich), 1-hydroxybenzotriazole hydrate (5.0 mg, 0.037 mmol, Aldrich), followed by acetic acid (2.3 mg, 0.034 mmol). The reaction mixture was stirred overnight at room temperature, taken up in ethyl acetate (15 mL), washed with brine and evaporated. The crude product was purified on silica gel with 95:5 of dichloromethane/methanol to give 1-[4-[4-amino-5-(2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidin-1-yl]-ethanone (11.2 mg). HRMS, observed: 370.1875; Calcd for (M+H)+: 370.1874.

Aufarbeitung

  1. washwashed with brine
  2. customevaporated
  3. customThe crude product was purified on silica gel with 95:5 of dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-06695398d61e4a65b7557d87feea64df
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615634B2

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