1-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one → 1-(4-Amino-quinazolin-7-ylmethyl)-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

HRID 1433060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433060
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[C@@H:15]([CH2:29][CH2:30][S:31][CH3:32])[C:14]3=[O:33])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1>Br.C(O)(=O)C.CCOCC>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][C@@H:15]([CH2:29][CH2:30][S:31][CH3:32])[C:14]3=[O:33])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 1

HCID 690288501-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

Produkt 1

HCID 670141251-(4-Amino-quinazolin-7-ylmethyl)-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-oneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 260Hydrogen BromideLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one (100 mg, 0.215 mmol) is dissolved in 5 ml of 30% hydrogen bromide in acetic acid. The mixture is stirred for 1 hour, diluted with ethyle ether. The ether is decanted and the resulting solid is washed thoroughly with ethyle ether. The resulting crude product is purified by column chromatography eluting with a 4/2/1 mixture of CH2Cl2/MeOH/NH4OH (30% in H2O). with a gradient of 5% MeOH:CH2Cl2 to 10% MeOH:CH2Cl2. The resulting product is purified by another column chromatography eluting with a gradient of 20% MeOH:CH2Cl2 to 50% MeOH:CH2Cl2. The title bound (30 mg, 42% yield) is obtained as an off-white solid.

Aufarbeitung

  1. customThe ether is decanted
  2. washthe resulting solid is washed thoroughly with ethyle ether
  3. customThe resulting crude product is purified by column chromatography
  4. washeluting with a 4/2/1 mixture of CH2Cl2/MeOH/NH4OH (30% in H2O)
  5. customThe resulting product is purified by another column chromatography
  6. washeluting with a gradient of 20% MeOH
  7. customis obtained as an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-dd90b56c3fbe4e41b3c761cc6d155dbc
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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