2-Phenylisobutyric acid → HCID 178476565, Verbindung

HRID 432341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432341
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][CH:3]=1.[CH3:31][C:32]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:36])[C:33]([OH:35])=[O:34].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:33]([OH:35])(=[O:34])[CH3:32].[C:33]([OH:35])(=[O:34])[CH3:32].[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:33](=[O:34])[C:32]([CH3:31])([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH3:36])=[CH:7][CH:6]=3)[C:16]=12

Komponenten

7

Edukt 5

HCID 132222-Phenylisobutyric acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178480983HCID 178480983, Verbindung

Produkt 1

HCID 178476565HCID 178476565, VerbindungAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution containing cis-3-(4-aminophenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.1 g, 0.000246 mol), α,α-dimethylphenylacetic acid (0.045 g, 0.000271 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.071 g, 0.000369 mol) and 1-hydroxy-7-azabenzotriazole (0.0037 g, 0.000271 mol) in anhydrous N,N-Dimethylformamide (5 mL) was stirred for 5 min., N,N-diisopropylethylamine (0.098 g, 0.00076 mol) was added dropwise and stirring under an atmosphere of nitrogen was continued for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-N1-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-2-methyl-2-phenylpropanamide diacetate (0.014 g, 0.000021 mol) as a white solid.

Aufarbeitung

  1. stirringstirring under an atmosphere of nitrogen
  2. waitwas continued for 16 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-8e319b70ee7f4e1197b08c4f93704ca8
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

Notizen zur Reaktion

Wird geladen…