m-Chloroperbenzoic acid → 3-(1,3-Benzoxazol-2-yl)-5-[1-(1-methyl-1-oxido-piperidin-1-ium-4-yl)pyrazol-4-yl]pyridin-2-amine

HRID 908375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908375
ClC1C=C(C(OO)=[O:9])C=CC=1.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:22]([NH2:39])=[N:23][CH:24]=[C:25]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)[CH:31]=2)[CH:26]=1>C(Cl)Cl>[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:22]([NH2:39])=[N:23][CH:24]=[C:25]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:33][CH2:34][N+:35]([CH3:38])([O-:9])[CH2:36][CH2:37]3)[CH:31]=2)[CH:26]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 425993593-(1,3-Benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine

Produkt 1

HCID 866301463-(1,3-Benzoxazol-2-yl)-5-[1-(1-methyl-1-oxido-piperidin-1-ium-4-yl)pyrazol-4-yl]pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Chlorobenzenecarboperoxoic acid (0.046 g) was added to 3-(1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine (0.100 g) in DCM (10 ml). The resulting solution was stirred for 5 minutes. The resultant precipitate was collected by filtration, washed with DCM (2 ml) and dried under vacuum. The residue was purified by SCX ion exchange chromatography (elution with 7M methanolic ammonia) and there was thus obtained 3-(1,3-benzoxazol-2-yl)-5-[1-(1-methyl-1-oxido-piperidin-1-ium-4-yl)pyrazol-4-yl]pyridin-2-amine (0.026 g); Mass Spectrum: M+H+ 391.29; RT 1.18 min; NMR Spectrum: (DMSOd6) 8.49 (d, 1H), 8.41 (d, 1H), 8.32 (s, 1H), 7.88 (s, 1H), 7.78 (dd, 1H), 7.73 (dd, 1H), 7.57 (br s, 2H), 7.38 (m, 2H), 4.26 (tt, 1H), 3.46 (m, 2H), 3.11 (s, 3H), 3.06 (m, 2H), 2.68 (m, 2H), 1.90 (br m, 2H).

Aufarbeitung

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with DCM (2 ml)
  3. customdried under vacuum
  4. customThe residue was purified by SCX ion exchange chromatography (elution with 7M methanolic ammonia) and there
  5. customRT 1.18 min

Quellen und Nachweise

ORD-Eintrag
ord-3c94da2a089d476ca493392fe87662ff
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017611B2

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