Lithium hydroxide, monohydrate → 3-[[[4-(2-Amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid

HRID 1353471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1353471
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29]C)=[O:28])[CH2:22]3)=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:31])=[CH:7][CH:8]=2)[N:3]=1.O[Li].O>C1COCC1.O>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([OH:29])=[O:28])[CH2:22]3)=[O:19])[CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:31])=[CH:7][CH:8]=2)[N:3]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86591808HCID 86591808, Verbindung

Produkt 1

HCID 211015923-[[[4-(2-Amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-[[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-cyclohexanecarboxylic acid, methyl ester (150 mg, 0.33 mmol) in THF (20 mL) and water (6 mL) was added LiOH.H2O (28.0 mg). The reaction mixture was stirred at rt overnight, and then solvent was evaporated in vacuo. The resulting residue was acidified to pH 4, the precipitate was collected by filtration and dried to afford the title product. LC-MS: 432 (M++1). 1H NMR (DMSO-d6) δ 1.10 (m, 2H), 1.25 (m, 2H), 1.75 (m, 3H), 1.95 (m, 1H), 2.25 (m, 1H), 3.10 (m, 4H), 3.50 (m, 5H), 6.25 (s, 1H), 6.40 (d, 1H), 7.25 (m, 1H), 7.50 (s, 1H), 780 (d, 1H).

Aufarbeitung

  1. customsolvent was evaporated in vacuo
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-85136c37e098488180db8b9031c5cbc8
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220856B2

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