4-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid → N-(3-fluoro-4-(3-(1-isopropylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

HRID 2241429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241429
[NH2:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[N:13](CC4C=CC(OC)=CC=4)[N:14]=[C:15]([NH:16][CH:17]4[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]4)[C:8]=23)=[C:4]([F:37])[CH:3]=1.[F:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH:50]=[CH:49][N:48]=[C:47]([C:51]([OH:53])=O)[C:46]2=[O:54])=[CH:41][CH:40]=1>>[F:37][C:4]1[CH:3]=[C:2]([NH:1][C:51]([C:47]2[C:46](=[O:54])[N:45]([C:42]3[CH:41]=[CH:40][C:39]([F:38])=[CH:44][CH:43]=3)[CH:50]=[CH:49][N:48]=2)=[O:53])[CH:36]=[CH:35][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][N:14]=[C:15]([NH:16][CH:17]3[CH2:18][CH2:19][N:20]([CH:23]([CH3:24])[CH3:25])[CH2:21][CH2:22]3)[C:8]=12

Komponenten

3

Edukt 2

HCID 673494894-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acidHCID 685133694-(4-amino-2-fluorophenoxy) N-(1-isopropylpiperidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-amine

Produkt 1

HCID 59304389N-(3-fluoro-4-(3-(1-isopropylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamideAusbeute 64 %

Versuchsvorschrift

Prepared by a 2-step process from 4-(4-amino-2-fluorophenoxy) N-(1-isopropylpiperidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (prepared as described in Example 101, Step A except using 1-isopropylpiperidin-4-amine) and 4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid (Example 125, Step E) according to the procedure of Example 101, Step B. The crude was rinsed with Et2O to afford 4.6 mg (64%) of the desired product. The desired product was treated with 2N HCl (Et2O solution) in a solution of MeOH and EtOAc to afford HCl salt compound. LRMS (APCIpos) m/e 601.3 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.17 (d, 1H), 8.06 (dd, 1H), 7.91 (d, 1H), 7.84 (d, 1H), 7.55 (m, 2H), 7.49 (d, 1H), 7.34 (t, 3H), 6.14 (d, 1H), 3.93 (m, 1H), 3.52 (m, 2H), 3.17 (m, 2H), 2.47 (m, 2H), 1.96 (m, 2H), 1.40 (d, 6H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −111.0, −127.6.

Aufarbeitung

  1. washThe crude was rinsed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-9635cbd4de6d412d9fe2e85f432cc04b
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723330B2

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