Lithium hydroxide, monohydrate → HCID 10434480, Verbindung

HRID 2250164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250164
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([C:39]([O:41]C)=[O:40])[NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[NH:30][C:29]4=[O:38])[CH2:24][CH2:23]3)=[O:21])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=O)(C)(C)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[NH:30][C:29]4=[O:38])[CH2:24][CH2:23]3)=[O:21])[C:39]([OH:41])=[O:40])=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58864391HCID 58864391, Verbindung

Produkt 1

HCID 10434480HCID 10434480, VerbindungAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5-(2-methoxycarbonyl-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-ethyl)-indazole-1-carboxylic acid tert-butyl ester (168 mg, 0.29 mmol) was dissolved in tetrahydrofuran (5 mL) in methanol (5 mL) was cooled to 0° C. A solution of lithium hydroxide monohydrate (49 mg, 2.04 mmol) in water (5 mL) was added. The reaction mixture was stirred at 0° C. for 6 h and then placed in the freezer for a further 16 h. The solvents were removed in vacuo and the residue dissolved in water (15 mL). The pH of the aqueous solution was adjusted to ca. 1 with 1N hydrochloric acid. The resulting white solid precipitated was collected by filtration. The solid was dried under vacuum to give the title compound (108 mg, 80%). 1H-NMR (DMSO-d6, 300 MHz) δ 12.94 (bs, 1H), 9.19 (s, 1H), 8.01 (s, 1H), 7.61 (s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.28 (dd, J=8.5 , 1.5 Hz, 1H), 7.13-7.06 (m, 2H), 6.86 (t, J=7.0 Hz, 1H), 6.76-6.72 (m, 2H), 4.32-4.24 (m, 2H), 4.09-4.02 (m, 4H), 3.17-2.97 (m, 2H), 2.72-2.59 (m, 2H), 1.57-1.35 (m, 4H). IR (KBr, cm−1) 3424, 2963, 2930, 1660, 1628, 1505, 1474, 1446, 753. Mass spec.: 463 (MH)+.

Aufarbeitung

  1. waitplaced in the freezer for a further 16 h
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue dissolved in water (15 mL)
  4. customThe resulting white solid precipitated
  5. filtrationwas collected by filtration
  6. customThe solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-777b4432e1e14fc8892b8b6ec3f0b277
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314883B2

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