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Cesium carbonate → Trifluoroacetic acid

HRID 511499
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 511499
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:13][C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:17]=[C:16]([NH:24][C:25]3[CH:39]=[CH:38][C:28]([CH2:29][P:30](=[O:37])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])=[CH:27][CH:26]=3)[N:15]=2)=[C:6]2[C:10]=1[CH2:9][N:8]([CH3:11])[C:7]2=[O:12].C([O:44][C:45](=[O:53])[CH2:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:100]([O-:103])([O-])=[O:101].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:35]([O:34][P:30]([CH2:29][C:28]1[CH:38]=[CH:39][C:25]([NH:24][C:16]2[N:15]=[C:14]([NH:13][C:5]3[CH:4]=[CH:3][C:2]([N:50]4[CH2:51][CH2:52][N:47]([CH2:46][C:45]([OH:53])=[O:44])[CH2:48][CH2:49]4)=[C:10]4[C:6]=3[C:7](=[O:12])[N:8]([CH3:11])[CH2:9]4)[C:19]([C:20]([F:21])([F:23])[F:22])=[CH:18][N:17]=2)=[CH:26][CH:27]=1)([O:31][CH2:32][CH3:33])=[O:37])[CH3:36].[F:21][C:20]([F:23])([F:22])[C:100]([OH:103])=[O:101]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2757326tert-Butyl 2-piperazinoacetateHCID 58292897Diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate

Produkt 2

HCID 6422Trifluoroacetic acid
HCID 58292968
HCID 58292968, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate (200.0 mg, 0.3183 mmol), piperazine-1-acetic acid tert-butyl ester (382 mg, 1.91 mmol), bis(dibenzylideneacetone)palladium (58.29 mg, 0.06366 mmol), 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (118.9 mg, 0.1910 mmol), Cs2CO3 (0.3111 g, 0.9548 mmol) in 1,4-dioxane (20 mL) was evacuated and purged with nitrogen three times. The mixture was stirred at 100° C. for 2 days. The crude mixture was purified by MDP. The purified ester was taken up in methylene chloride (1.2 mL) and trifluoroacetic acid (0.6 mL) and the mixture was stirred at room temperature for 3 hours. The crude product was purified by MDP to obtain the title compound as a trifluoroacetic acid salt. 1H NMR (400 MHz, methanol-d4) δ=1.27 (t, J=7.1 Hz, 6 H), 3.19 (s, 3 H), 3.29 (d, J=21.5 Hz, 2 H), 3.41 (br. s., 4 H), 3.60 (br. s., 4 H), 4.07 (qd, J=7.2, 6.9 Hz, 4 H), 4.17 (s, 2 H), 4.51 (s, 2 H), 7.26 (d, J=9.1 Hz, 1 H), 7.34 (d, J=6.6 Hz, 2 H), 7.57 (d, J=7.8 Hz, 2 H), 8.36 (s, 1 H), 8.69 (br. s., 1 H). MS (ES+): m/z 692.27 (100) [MH+]; HPLC: tR=0.78 min (UPLC, purity).

Aufarbeitung

  1. customwas evacuated
  2. custompurged with nitrogen three times
  3. customThe crude mixture was purified by MDP
  4. stirringtrifluoroacetic acid (0.6 mL) and the mixture was stirred at room temperature for 3 hours
  5. customThe crude product was purified by MDP

Quellen und Nachweise

ORD-Eintrag
ord-568e837218e047cab6d3a01932a91e45
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096624B2

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