Acetic Acid → 5-{5-[[(Acetyloxy)imino](amino)methyl]-2-isobutoxy-3-pyridinyl}-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354186

Reaktionsgleichung

Reaktionsgleichung von HRID 354186
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:9]([C:11]2[NH:12][C:13](=[O:24])[C:14]3[C:15](=[C:17]([CH2:21][CH2:22][CH3:23])[N:18]([CH3:20])[N:19]=3)[N:16]=2)[CH:10]=1)=[NH:4].[C:30](O)(=[O:32])[CH3:31].Cl.CN(C)CCCN=C=NCC>O1CCOCC1>[C:30]([O:1][N:2]=[C:3]([NH2:4])[C:5]1[CH:10]=[C:9]([C:11]2[NH:12][C:13](=[O:24])[C:14]3[C:15](=[C:17]([CH2:21][CH2:22][CH3:23])[N:18]([CH3:20])[N:19]=3)[N:16]=2)[C:8]([O:25][CH2:26][CH:27]([CH3:28])[CH3:29])=[N:7][CH:6]=1)(=[O:32])[CH3:31]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178438342HCID 178438342, Verbindung

Produkt 1

HCID 1363883775-{5-[[(Acetyloxy)imino](amino)methyl]-2-isobutoxy-3-pyridinyl}-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-Hydroxy-6-isobutoxy-5-(2-methyl-7-oxo-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-5-yl)-3-pyridinecarboximidamide (Example 39) (65 mg, 0.16 mmol), N,N-dimethylaminopyridine (24 mg, 0.20 mmol), acetic acid (9.7 mg, 0.16 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (37.5 mg, 0.20 mmol) were stirred in dioxan (2 mL) for 14 h. The solvent was removed in vacuo and the product purified by flash column chromatography (eluting with 90% dichloromethane:methanol) to give the product (58 mg) as a white solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe product purified by flash column chromatography (eluting with 90% dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-55cd0daca4644c1eabd30e8b1ef305d7
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756373B1

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