Acetic Acid → [4-({[3-(8-Methyl-3-phenylcinnolin-4-yl)phenyl]amino}methyl)phenyl]acetic acid

HRID 643296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643296
C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[C:28]4[C:23](=[C:24]([CH3:29])[CH:25]=[CH:26][CH:27]=4)[N:22]=[N:21][C:20]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:14]=2)=[CH:7][CH:6]=1.O.[OH-].[Li+].C(O)(=O)C>C1COCC1.CO.O>[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]=[N:21][C:20]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:19]2[C:15]1[CH:14]=[C:13]([NH:12][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:36])=[O:2])=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68579431(4-{[3-(8-Methyl-3-phenyl-cinnolin-4-yl)-phenylamino]-methyl}-phenyl)-acetic acid methyl ester

Produkt 1

HCID 11856166[4-({[3-(8-Methyl-3-phenylcinnolin-4-yl)phenyl]amino}methyl)phenyl]acetic acidAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a stirred solution of (4-{[3-(8-methyl-3-phenyl-cinnolin-4-yl)-phenylamino]-methyl}-phenyl)-acetic acid methyl ester in THF/methanol/water (2:1:1, 10 mL) was added lithium hydroxide monohydrate (0.1 g). The reaction was stirred at 40° C. for 1 hour. The reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and dried over P2O5 to give the title compound as an orange solid (0.02 g, 43% for Step 5 and Step 6). MS (ESI) m/z 460; HRMS (ESI, [M+H]+) 460.2012.

Aufarbeitung

  1. customthe solid was collected
  2. dry with materialdried over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-9c57935b3a274c209ffd398cdf61191f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700595B2

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