Acetic Acid → 2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(benzylamino)imidazo[4,5-b]pyridine

HRID 396382

Reaktionsgleichung

Reaktionsgleichung von HRID 396382
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13](Cl)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CC([O-])(C)C.[Na+].CC(O)=O>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([NH:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 224861525-Chloro-2-(4-fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)imidazo[4,5-b]pyridineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 98912922-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(benzylamino)imidazo[4,5-b]pyridineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-(chloro)imidazo[4,5-b]pyridine (100 mg; 0.25 mmol), R-(+)-BINAP (10 mg; 0.016 mmol), Pd2(dba)3 (22 mg; 0.024 mmol) are suspended in xylene (16 ml), benzylamine (0.53 ml; 4.9 mmol) is added, followed by NaOtBu (47 mg; 0.49 mmol) and heated to 160° C. for 10 min. under argon. The reaction mixture is poured on water (100 ml) containing HOAc (2 ml) and extracted with TBME three times. The combined organic phases are washed with 2N Na2CO3, dried over Na2SO4 and evaporated to dryness. Purification via SiO2 chromatography (TMBE/hexane 6:4 to 10:0) and recrystallisation from TBME yields the title compound as colorless crystals (50 mg: 50%).

Aufarbeitung

  1. additionThe reaction mixture is poured on water (100 ml)
  2. extractionextracted with TBME three times
  3. washThe combined organic phases are washed with 2N Na2CO3
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customPurification
  7. customvia SiO2 chromatography (TMBE/hexane 6:4 to 10:0) and recrystallisation from TBME

Quellen und Nachweise

ORD-Eintrag
ord-f7cdab4639dc4cb589fcc05a90336c40
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608072B1

Verknüpfte Notizen

Wird geladen…