5-Bromo-3-(1-ethyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one → 5-tert-Butyl-2-(3-(6-(1-ethyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-one

HRID 1772110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772110
Br[C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:12]=[N:13][N:14]([CH2:16][CH3:17])[CH:15]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C([O:21][CH2:22][C:23]1[C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH:26]=[CH:25][C:24]=1[N:38]1[CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:47]([CH3:50])([CH3:49])[CH3:48])[CH:44]=2)[C:39]1=[O:51])(=O)C>>[C:47]([C:43]1[CH:44]=[C:45]2[C:40](=[CH:41][CH:42]=1)[C:39](=[O:51])[N:38]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([C:2]3[N:3]=[C:4]([NH:10][C:11]4[CH:12]=[N:13][N:14]([CH2:16][CH3:17])[CH:15]=4)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=3)[C:23]=1[CH2:22][OH:21])[CH2:46]2)([CH3:50])([CH3:48])[CH3:49]

Komponenten

3

Edukt 2

HCID 580437415-Bromo-3-(1-ethyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-oneHCID 866979362-(5-tert-Butyl-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate

Produkt 1

HCID 569285505-tert-Butyl-2-(3-(6-(1-ethyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-oneAusbeute 48,2 %

Versuchsvorschrift

Using the same general procedure as Example 105, reaction of 111c (253 mg, 0.85 mmol) and 103f (473 mg, 1.02 mmol) afforded a 48% yield (210 mg) of 111 as an off-white solid: mp 138-140° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.57 (s, 1H), 8.17 (s, 1H), 7.72 (m, 3H), 7.61 (m, 2H), 7.51 (t, 1H, J=7.6 Hz), 7.43 (m, 1H), 7.31 (s, 1H), 4.94 (s, 2H), 4.88 (t, 1H, J=5.0 Hz), 4.49 (d, 2H, J=5.0 Hz), 4.06 (q, 2H, J=7.1 Hz), 3.52 (s, 3H), 1.37 (s, 9H), 1.33 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 513.2 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-960f2a490ac84a10ba2baac34db36574
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249123B2

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