1-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)-2-phenylethanone → 2-Phenyl-1-{7-[4-(4-(pyrrolidin-1-yl)piperidine-1-carbonyl)phenyl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl}-ethanone

HRID 659383

Reaktionsgleichung

Reaktionsgleichung von HRID 659383
I[C:2]1[CH:20]=[N:19][C:5]2[NH:6][CH2:7][CH2:8][N:9]([C:10](=[O:18])[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[N:21]1([CH:26]2[CH2:31][CH2:30][N:29]([C:32]([C:34]3[CH:39]=[CH:38][C:37](B4OC(C)(C)C(C)(C)O4)=[CH:36][CH:35]=3)=[O:33])[CH2:28][CH2:27]2)[CH2:25][CH2:24][CH2:23][CH2:22]1>>[C:12]1([CH2:11][C:10]([N:9]2[CH2:8][CH2:7][NH:6][C:5]3[N:19]=[CH:20][C:2]([C:37]4[CH:38]=[CH:39][C:34]([C:32]([N:29]5[CH2:28][CH2:27][CH:26]([N:21]6[CH2:22][CH2:23][CH2:24][CH2:25]6)[CH2:31][CH2:30]5)=[O:33])=[CH:35][CH:36]=4)=[CH:3][C:4]2=3)=[O:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 578859371-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)-2-phenylethanoneHCID 57886103[4-(Pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone

Produkt 1

HCID 578858872-Phenyl-1-{7-[4-(4-(pyrrolidin-1-yl)piperidine-1-carbonyl)phenyl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl}-ethanoneAusbeute 52 %

Versuchsvorschrift

1-(7-Iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)-2-phenylethanone (30 mg) was reacted with (4-(pyrrolidin-1-yl)piperidin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]methanone as in General Procedure 4A to give the title compound as a white foam (52% yield). M.p. (foam), LCMS: m/z=510.13 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.47-1.62 (m, 2H), 1.75-2.05 (m, 3H), 2.22-2.29 (m, 1H), 2.53-2.62 (m, 5H), 2.82-3.10 (m, 3H), 3.33-3.52 (m, 2H), 3.71-3.88 (m, 3H), 3.95 (s, 2H), 4.51-4.63 (m, 1H), 5.25 (bs, 1H), 7.12-7.34 (m, 5H), 7.35-7.48 (m, 4H), 8.16 (s, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-2d45f40aeb494066a370d5ba371cbecb
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080561B2

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