Citric Acid → 4-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid

HRID 1516442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516442
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:27]4[C:22](=[C:23]([Br:28])[CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO.O>[Br:28][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:22]=1[CH:21]=[CH:20][N:19]2[C:17]1[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)[N:18]=1

Komponenten

7

Edukt 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 686055994-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester

Produkt 1

HCID 674356194-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexane-carboxylic acid ethyl ester (5.8 g) and LiOH.H2O (1.65 g) in THF (100 mL), EtOH (40 mL) and H2O (30 mL) was stirred at RT overnight. The reaction mixture was then acidified with citric acid (7.54 g in 20 mL H2O), and stirred at RT for 1 h. The precipitate was filtered, washed with water, then Et2O, and dried to provide 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid (5.27 g, 97%) as a white powder.

Aufarbeitung

  1. stirringstirred at RT for 1 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialEt2O, and dried

Quellen und Nachweise

ORD-Eintrag
ord-67f8480cacb843d6971463a77acdfadd
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227478B2

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