Ammonia → 2-[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetamide

HRID 1992645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992645
C([O:5][C:6](=O)[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:9]=1)(C)(C)C.C(C1NC=CN=1)(C1[NH:26]C=CN=1)=O.N>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:14][C:13]1[C:8]([CH2:7][C:6]([NH2:26])=[O:5])=[CH:9][C:10]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[N:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66869033[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid tert-butyl ester

Produkt 1

HCID 668699142-[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

[5-Methyl-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid tert-butyl ester (320 mg, 1.05 mmol) is dissolved in a mixture of TFA and CH2Cl2 (10 ml/10 ml) and stirred at RT. After 1 h at RT, TLC analysis indicated complete conversion of starting material. The solvent is removed by rotary evaporation, and replaced by dry DMF (1.5 ml). Under an atmosphere of argon, carbonyl diimidazole (187 mg, 1.16 mmol) is added. After 30 minutes at RT, TLC analysis indicated complete conversion of the carboxylic acid. An aqueous solution of ammonia (25%, 16 ml) is added at RT. After 15 minutes at RT, solvents are removed under high vacuum. The residue is dissolved in CH2Cl2/MeOH (9:1) and purified by FCC (CH2Cl2/MeOH, slow gradient from 95:5 to 40:60) to yield the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 2.07 (s, 3H), 2.38 (s, 3H), 2.64 (s, broad, 4H), 3.34 (s, 2H), 3.46 (s, broad, 4H), 6.72 (s, 1H), 6.95 (s, broad, 1H), 7.44 (s, broad, 1H), 7.87 (s, 1H). ES+−MS: 249.3 [M+H]+, ES−−MS: 247.3 [M−H]−.

Aufarbeitung

  1. customThe solvent is removed by rotary evaporation
  2. waitAfter 30 minutes at RT
  3. waitAfter 15 minutes at RT
  4. customsolvents are removed under high vacuum
  5. dissolutionThe residue is dissolved in CH2Cl2/MeOH (9:1)
  6. custompurified by FCC (CH2Cl2/MeOH, slow gradient from 95:5 to 40:60)

Quellen und Nachweise

ORD-Eintrag
ord-ee3bf67ea38049e1ba9e53c9f237b981
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648989B2

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