(3R)-3-Aminopiperidine, 3-BOC protected → (R)-3-(3-aminopiperidin-1-yl)-1-methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2(1H)-one

HRID 57959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57959
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7]C(=O)OC(C)(C)C)[CH2:2]1.Br[C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20](Br)[N:21]=1.Cl[C:26]1[N:31]=[CH:30][C:29]2[CH:32]=[N:33][NH:34][C:28]=2[CH:27]=1.[CH3:35][N:36]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[N:37]1>>[NH2:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:16]2[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([N:34]3[C:28]4[CH:27]=[C:26]([C:39]5[CH:38]=[N:37][N:36]([CH3:35])[CH:40]=5)[N:31]=[CH:30][C:29]=4[CH:32]=[N:33]3)[N:21]=2)[CH2:2]1

Komponenten

5

Edukt 4

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Produkt 1

HCID 86707141(R)-3-(3-aminopiperidin-1-yl)-1-methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2(1H)-oneAusbeute 17,9 %

Versuchsvorschrift

Following the procedures as described in Example 124 and starting with (R)-tert-butyl piperidin-3-ylcarbamate, 3,5-dibromo-1-methylpyrazin-2(1H)-one, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 243 was obtained as a yellow solid (58 mg, 17.9%) over four steps. 1H NMR (500 MHz, DMSO-d6) δ9.09 (s, 1H), 8.45 (s, 1H), 8.37 (s, 1H), 8.32 (s, 1H), 8.05 (s, 1H), 7.64 (s, 1H), 4.59-4.72 (m, 2H), 3.92 (s, 3H), 3.51 (s, 3H), 2.98-3.06 (m, 1H), 2.80-2.92 (m, 1H), 2.80-2.81 (m, 1H), 1.92-1.94 (m, 1H), 1.78-1.79 (m, 1H), 1.60-1.62 (m, 1H), 1.29-1.34 (m, 1H); MS (ESI) m/z: 406 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-6e61ed6a146f48fbb8edc8eec556b376
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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