L-Proline → 5-[1-(1,1-dimethyl-propyl)-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

HRID 1966779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966779
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:20])[C:11]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][CH3:17])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[N:21]1([C:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=O)[CH:25]=[N:24][CH:23]=[N:22]1.N1CCC[C@H]1C(O)=O>CO>[CH3:18][C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:20]=[C:28]1[C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=1[N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)([CH3:19])[CH2:16][CH3:17]

Komponenten

5

Edukt 3

HCID 145742L-ProlineHCID 35364462-(1H-1,2,4-Triazol-1-yl)benzaldehydeHCID 585419944-(2-amino-pyrimidin-5-yl)-N1-(1,1-dimethyl-propyl)-benzene-1,2-diamine

Produkt 1

HCID 585419115-[1-(1,1-dimethyl-propyl)-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A reaction mixture of 4-(2-amino-pyrimidin-5-yl)-N1-(1,1-dimethyl-propyl)-benzene-1,2-diamine (130 mg, 0.48 mmol), 2-1,2,4-triazol-1-yl-benzaldehyde (110 mg, 0.64 mmol) and L-proline (5 mg) in MeOH (25 mL) is refluxed for 16 hours. The reaction mixture is allowed to cool to room temperature and is concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography with 8% MeOH in CH2Cl2 as the eluent to afford 5-[1-(1,1-dimethyl-propyl)-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine. LCMS (ESMS): m/z 425.20 (M++1)

Aufarbeitung

  1. temperatureis refluxed for 16 hours
  2. concentrationis concentrated under reduced pressure
  3. customThe residue is purified by silica gel flash column chromatography with 8% MeOH in CH2Cl2 as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-9accef7ca1eb4f4aa9a530f69394f5f5
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420655B2

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