Triphenylphosphine → 3-(4-Methylpiperazin-1-yl)propyl [3-(5-methyl-2-oxooxazolo-[4,5-b]pyridin-3-ylmethyl)phenyl]carbamate

HRID 655312

Reaktionsgleichung

Reaktionsgleichung von HRID 655312
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1.O[CH2:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:33])[O:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)[CH:17]=[CH:18][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:33])[O:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]4)[CH:17]=[CH:18][CH:19]=3)[C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 100120755-Methyloxazolo[4,5-b]pyridin-2(3H)-oneHCID 595647273-(4-Methylpiperazin-1-yl)propyl (3-hydroxymethylphenyl)carbamate

Produkt 1

HCID 595647153-(4-Methylpiperazin-1-yl)propyl [3-(5-methyl-2-oxooxazolo-[4,5-b]pyridin-3-ylmethyl)phenyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

98 mg (0.65 mmol) of 5-methyl-3H-oxazolo[4,5-b]pyridin-2-one, 200 mg (0.65 mmol) of 3-(4-methylpiperazin-1-yl)propyl (3-hydroxymethylphenyl)carbamate and 325 mg (0.98 mmol) of polymer-bound triphenylphosphine (3 mmol/g) are suspended in 5 ml of DMF, and the mixture is shaken for 30 min. 229 mg (0.98 mmol) of di-tert-butyl azodicarboxylate are subsequently added. The reaction mixture is shaken at room temperature. The reaction mixture is filtered and rinsed with THF, and the filtrate is evaporated. The residue is purified by column chromatography on silica gel.

Aufarbeitung

  1. stirringThe reaction mixture is shaken at room temperature
  2. filtrationThe reaction mixture is filtered
  3. washrinsed with THF
  4. customthe filtrate is evaporated
  5. customThe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-829cde76b514485e9a04d8c2ab01967f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071593B2

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