tert-Butyl piperazine-1-carboxylate → (R)-3-hydroxymethyl-4-[6-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 82036

Reaktionsgleichung

Reaktionsgleichung von HRID 82036
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:31]([OH:33])=O)[C:11]3[C:16](/[CH:17]=[CH:18]/[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][N:14]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.C(N1CCNCC1)(OC(C)(C)C)=O.[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][NH:57][C@@H:56]([CH2:60][OH:61])[CH2:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48]>>[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][N:57]([C:31]([C:10]2[C:11]3[C:16](/[CH:17]=[CH:18]/[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][N:14]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:12]=3[N:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[CH:9]=2)=[O:33])[C@@H:56]([CH2:60][OH:61])[CH2:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48]

Komponenten

4

Edukt 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 1363594996-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Produkt 1

HCID 136359500(R)-3-hydroxymethyl-4-[6-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 28 %

Versuchsvorschrift

Utilizing the procedure described in example 1.6 except substituting 6-chloro-3-[(E)-2-(4-chloro-phenyl)-vinyl]-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid with 6-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid and 1-boc-piperazine with (R)-3-hydroxymethyl-piperazine-1-carboxylic acid tert-butyl ester, (R)-3-hydroxymethyl-4-[6-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.16 g, 28%) was obtained as a yellow solid.

Quellen und Nachweise

ORD-Eintrag
ord-c1dfbc4b02af46b2aca30245b27f8451
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846712B2

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