Trifluoroacetic acid methylene chloride → HCID 178488197, Verbindung

HRID 432407

Reaktionsgleichung

Reaktionsgleichung von HRID 432407
FC(F)(F)C(O)=O.ClCCl.[NH2:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([CH:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]4)[CH2:35][CH2:34]3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(=O)[O-])=[C:23]([O:31][CH3:32])[CH:22]=3)[C:13]=12>ClCCl>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:13]3[C:14](=[N:15][CH:16]=[N:17][C:12]=3[NH2:11])[N:18]([C@H:33]3[CH2:38][CH2:37][C@@H:36]([N:39]4[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]4)[CH2:35][CH2:34]3)[N:19]=2)=[CH:22][C:23]=1[O:31][CH3:32]

Komponenten

4

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22346847N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)carbamate

Produkt 1

HCID 178488197HCID 178488197, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of trifluoroacetic acid/dichloromethane (20:80, 200 mL) was added to a solution of N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)carbamate(10.85 g, 20.24 mmol) in dichloromethane (100 mL) at 0° C. 2 hours later, the ice-bath was removed and the solvents were evaporated and the residue was dissolved in dichloromethane. Sodium hydroxide (1.0N) was added to adjust the pH to about 10. The solid formed upon removal of organic solvent was collect by filtration to give cis-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (8.84 g, 100%). 1H NMR (CDCl3) δ 1.65 (m, 2H), 1.83 (m, 2H), 2.18 (m, 2H), 2.31 (s, 3H), 2.35-2.60 (m, 11H), 3.90 (s, 3H), 4.00 (bs, 2H), 4.89 (m, 1H), 5.61 (bs, 2H), 6.83 (d, J=7.78 Hz, 1H), 7.12 (m, 2H), 8.35 (s, 1H).

Aufarbeitung

  1. custom2 hours later, the ice-bath was removed
  2. customthe solvents were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionSodium hydroxide (1.0N) was added
  5. customThe solid formed upon removal of organic solvent
  6. filtrationwas collect by filtration

Quellen und Nachweise

ORD-Eintrag
ord-6e50901cc7cd45cc9c7d2d29bfadf365
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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