Trifluoroacetic acid methylene chloride → HCID 22346761, Verbindung

HRID 432295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432295
FC(F)(F)C(O)=O.ClCCl.[NH2:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([CH:37]3[CH2:42][CH2:41][N:40]([CH2:43][C:44]4[NH:45][CH:46]=[CH:47][N:48]=4)[CH2:39][CH2:38]3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(=O)OC(C)(C)C)=[C:23]([O:35][CH3:36])[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]([CH:37]3[CH2:42][CH2:41][N:40]([CH2:43][C:44]4[NH:45][CH:46]=[CH:47][N:48]=4)[CH2:39][CH2:38]3)[N:19]=2)=[CH:22][C:23]=1[O:35][CH3:36]

Komponenten

4

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22347020tert-butyl N-(4-{4-amino-1-[1-(1H-2-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)carbamate

Produkt 1

HCID 22346761HCID 22346761, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of trifluoroacetic acid/dichloromethane (20:80, 2 mL) was added to a solution of tert-butyl N-(4-{4-amino-1-[1-(1H-2-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)carbamate (55 mg, 0.106 mmol) in dichloromethane (0.5 mL) at 0° C. After 15 minutes, the ice-bath was removed and the reaction mixture was stirred at room temperature for 5 hours. Solvents were then evaporated and the residue was dissolved in dichloromethane. Saturated sodium bicarbonate was added to adjust the PH to about 8. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated give 3-(4-amino-3-methoxyphenyl)-1-[1-(1H-2-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 68%). 1H NMR (CDCl3-d) δ 2.20 (m, 2H), 2.44 (m, 2H), 3.04 (m, 2H), 3.75 (s, 2H), 3.93 (s, 3H), 4.01 (s, 2H), 4.80 (m, 1H), 5.58 (bs, 2H), 6.82 (m, 1H), 7.01 (m, 4H), 8.34 (s, 1H).

Aufarbeitung

  1. customthe ice-bath was removed
  2. customSolvents were then evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionSaturated sodium bicarbonate was added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with dichloromethane
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2612e02daa44496e91fd19e8ec57bff9
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

Notizen zur Reaktion

Wird geladen…