Trifluoroacetic acid → 1-butyl-3-(3-cyclobutyl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

HRID 571407

Reaktionsgleichung

Reaktionsgleichung von HRID 571407
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH:30]3[CH2:33][CH2:32][CH2:31]3)=[N:9][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:4]=2[CH:3]=1.[CH2:34]([NH:38][C:39]([NH2:41])=[O:40])[CH2:35][CH2:36][CH3:37].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+].C(O)(C(F)(F)F)=O>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[CH2:34]([NH:38][C:39]([NH:41][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH:30]3[CH2:31][CH2:32][CH2:33]3)=[N:9][NH:10][C:4]=2[CH:3]=1)=[O:40])[CH2:35][CH2:36][CH3:37]

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 11595ButylureaHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 895258986-chloro-3-cyclobutyl-1-trityl-1H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 1784495461-butyl-3-(3-cyclobutyl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In a manner similar to that described in Scheme 6 and Example 30, 6-chloro-3-cyclobutyl-1-trityl-1H-pyrazolo[4,3-c]pyridine was reacted with 1-butylurea, (Xantphos, Pd(OAc)2, Cs2CO3, dioxane, 80° C., overnight) and then deprotected with TFA to provide 1-butyl-3-(3-cyclobutyl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea. MS ESI calc'd. for C15H21N5O[M+1]+ 288, found 288.

Quellen und Nachweise

ORD-Eintrag
ord-3e37506a019f4bb5993cea20e35b7220
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023865B2

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