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2-fluoro-6-({2-[(2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide → HCID 178492997, Verbindung

HRID 1014444
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1014444
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[C:13]3[CH:45]=[CH:44][N:43](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]=3[N:15]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][CH:28]([N:31]5[CH2:36][CH2:35][N:34]([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:33][CH2:32]5)[CH2:27][CH2:26]4)=[CH:21][C:20]=3[O:41][CH3:42])[N:17]=2)[C:3]=1[C:4]([NH2:6])=[O:5]>O1CCOCC1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][CH:28]([N:31]5[CH2:36][CH2:35][N:34]([S:37]([CH3:40])(=[O:38])=[O:39])[CH2:33][CH2:32]5)[CH2:27][CH2:26]4)=[CH:21][C:20]=3[O:41][CH3:42])[NH:15][C:14]3=[N:43][CH:44]=[CH:45][C:13]=23)[C:3]=1[C:4]([NH2:6])=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 594421352-fluoro-6-({2-[(2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide

Produkt 1

HCID 178492997HCID 178492997, VerbindungAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A suspension of 2-fluoro-6-({2-[(2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide (2.78 g, 3.51 mmol) and 1,4-dioxane (100 mL) in a 200 mL sealed flask was stirred in an 85° C. bath for 11 hours. The solution was extracted with ethyl acetate (200 mL) and brine (50 mL). The organic layers were dried over MgSO4, filtered, concentrated onto Celite and purified by SiO2 column chromatography (1-10% MeOH in CH2Cl2 and 0.1% NH4OH) to afford 2-fluoro-6-({2-[(2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-1H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide (1.0 g, 1.568 mmol, 44.7% yield). This material was combined in a 100mL round bottomed flask with approximately 600 mg of purified material from another batch. THF (10 mL) was added and the slurry was sonicated for 2 minutes. Ether (30 mL) was added and the slurry was sonicated for 2 minutes. The slurry was filtered and the solid collected. The solid was placed on the high vacuum pump at 0.5 torr for 2 hours to afford 2-fluoro-6-({2-[(2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-1H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide (1.4 g, 2.195 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48-1.56 (m, 2H), 1.79-1.82 (m, 2H), 2.34-2.39 (m, 1H), 2.57-2.62 (m, 6H), 2.82 (s, 3H), 3.05-3.08 (m, 4H), 3.62-2.65 (m, 2H), 3.77 (s, 3H), 6.17 (s, 1H), 6.43 (dd, J=2.2, 8.7 Hz, 1H), 6.59 (d, J=2.0 Hz, 1H), 6.85-6.91 (m, 2H), 7.34-7.40 (m, 2H), 7.86 (d, J=8.6 Hz, 1H), 7.97 (s, 1H), 8.05 (s, 1H), 8.44 (d, J=8.4 Hz, 1H), 10.41 (s, 1H), 11.26 (s, 1H); ESIMS (M+H)+=638.

Aufarbeitung

  1. customsealed flask
  2. extractionThe solution was extracted with ethyl acetate (200 mL) and brine (50 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated onto Celite
  6. custompurified by SiO2 column chromatography (1-10% MeOH in CH2Cl2 and 0.1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-d53b985339ef405287d86aac5aa27c09
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981903B2

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