Water → HCID 136337180, Verbindung

HRID 1428854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428854
O.[OH-].[Li+].O.C([O:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][C:19]4[CH2:28][CH2:27][CH2:26][C:20]=4[CH:21]=3)[N:16]=2)[CH:14]=1)=[O:9])C.C([O:31][C:32]([C:34]1[CH:35]=[N:36][N:37]([C:39]2[NH:48][C:47](=[O:49])[C:46]3[C:45]4[CH2:50][CH2:51][CH2:52][C:44]=4[CH:43]=[CH:42][C:41]=3[N:40]=2)[CH:38]=1)=[O:33])C>C1COCC1>[O:25]=[C:23]1[C:22]2[C:21]3[CH2:20][CH2:26][CH2:27][C:28]=3[CH:19]=[CH:18][C:17]=2[N:16]=[C:15]([N:13]2[CH:14]=[C:10]([C:8]([OH:7])=[O:9])[CH:11]=[N:12]2)[NH:24]1.[O:49]=[C:47]1[C:46]2[C:41](=[CH:42][C:43]3[CH2:44][CH2:52][CH2:51][C:50]=3[CH:45]=2)[N:40]=[C:39]([N:37]2[CH:38]=[C:34]([C:32]([OH:31])=[O:33])[CH:35]=[N:36]2)[NH:48]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 136337178HCID 136337178, VerbindungHCID 136337179HCID 136337179, Verbindung

Produkt 2

HCID 136027564HCID 136027564, VerbindungHCID 136337180HCID 136337180, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (0.611 g, 14.6 mmol) and water (9.1 mL) were added to a 10:1 mixture of 1-(4-oxo-4,6,7,8-tetrahydro-3H-cyclopenta[g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester and 1-(1-oxo-2,7,8,9-tetrahydro-1H-cyclopenta[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (1.18 g, 0.228 mmol) in THF (13.6 mL) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was redissolved in water (20 mL). This solution was brought to pH 1 with 1M aqueous HCl. The resulting precipitate was collected and dried to yield a 10:1 mixture of the titled compound and 1-(1-oxo-2,7,8,9-tetrahydro-1H-cyclopenta[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid (1.05 g, 98% yield). A portion of the precipitate (0.511 g) was triturated twice from 10 mL DMSO to yield a pure sample of the titled compound (0.310 g, 61% recovery). MS (ESI/Cl): mass calcd. for C15H12N4O3, 296.1; m/z found, 297.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.00 (s, 1H), 12.68 (s, 1H), 8.93 (s, 1H), 8.24 (s, 1H), 7.96 (s, 1H), 7.52 (s, 1H), 3.05-2.93 (m, 4H), 2.09 (p, J=7.4 Hz, 2H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was redissolved in water (20 mL)
  3. customThe resulting precipitate was collected
  4. customdried
  5. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-ad298c4d614b4d66bcb02a2183a999f2
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937078B2

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