Lithium hydroxide, monohydrate → 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid

HRID 1947017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947017
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]([O:28][CH2:29][CH2:30][CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])[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>C1COCC1.CO.O>[CH3:35][S:32]([CH2:31][CH2:30][CH2:29][O: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[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[N:18]=1)(=[O:34])=[O:33]

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 693084624-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

Produkt 1

HCID 580170794-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acidAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-yl-amino}-cyclohexanecarboxylic acid ethyl ester (35.4 g, 70 mmol) in THF (180 mL) and MeOH (200 mL) was added a solution of LiOH-H2O (14.69 g) in H2O (150 mL). The resulting mixture was briefly heated in a steam bath and stirred at RT with a mechanical stirrer for 1 h to provide a light yellow solution. The reaction mixture was concentrated in vacuo and diluted with cold H2O and the pH was adjusted to 6 with 10% HCl. The resulting solid was filtered, washed several times with cold H2O and finally with EtOH at 0° C. The resulting solid product was then dried in vacuo to provide 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclo-hexanecarboxylic acid (32.2 g, 97.4%).

Aufarbeitung

  1. temperatureThe resulting mixture was briefly heated in a steam bath
  2. customto provide a light yellow solution
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with cold H2O
  5. filtrationThe resulting solid was filtered
  6. washwashed several times with cold H2O
  7. customat 0° C
  8. customThe resulting solid product was then dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5494d0fe52334a7abc5b13ea22088dff
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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