m-Chloroperbenzoic acid → 2-(4-Fluorophenyl)-1-(2-(1-(s)-phenylethyl)amino-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

HRID 396380

Reaktionsgleichung

Reaktionsgleichung von HRID 396380
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:30]3[CH:35]=[CH:34][N:33]=[C:32](SC)[N:31]=3)[C:10]3[C:11]([N:29]=2)=[N:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[C:49]1([C@@H:55]([NH2:57])[CH3:56])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH:57][C@H:55]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH3:56])[N:31]=3)[C:10]3[C:11]([N:29]=2)=[N:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 758181-Phenethylamine, (-)-HCID 224861592-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

Produkt 1

HCID 213545192-(4-Fluorophenyl)-1-(2-(1-(s)-phenylethyl)amino-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridineAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21922555Acetic acid methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine (106 mg, 0.2 mmol) is dissolved in CH2Cl2/HOAc 1:1 (10 ml), combined with mCPBA (113 mg 70%, 0.24 mmol) and stirred for 15 min. The reaction mixture is poured on water and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4. filtered and evaporated to dryness to yield the crude sulfoxide (100 mg), which is dissolved in 1-(S)-phenylethylamine (0.2 ml) and heated to 120° C. for 1 h. Purification over SiO2 (acetone/hexanes 1:1) yielded the title compound as colorless foam (45 mg 35%)

Aufarbeitung

  1. additionThe reaction mixture is poured on water
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto yield the crude sulfoxide (100 mg), which
  7. customPurification over SiO2 (acetone/hexanes 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-01a57e2ac74e44b59c31bb25a522d7f1
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608072B1

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