Toluene → 2-Benzyloxycarbonylamino-3-{2-methoxy-5-methyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionic acid bis (trifluoroacetate)

HRID 1615960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615960
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][NH:21][C:22]1[C:27]([CH3:28])=[C:26]([N:29]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:44]=[CH:43][C:42]4[CH2:41][CH2:40][CH2:39][NH:38][C:37]=4[N:36]=3)[CH2:31][CH2:30]2)[N:25]=[C:24]([O:45][CH3:46])[N:23]=1)[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][NH:21][C:22]1[C:27]([CH3:28])=[C:26]([N:29]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:44]=[CH:43][C:42]4[CH2:41][CH2:40][CH2:39][NH:38][C:37]=4[N:36]=3)[CH2:31][CH2:30]2)[N:25]=[C:24]([O:45][CH3:46])[N:23]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 66641154Tert-butyl 2-benzyloxycarbonylamino-3-{2-methoxy-5-methyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-pyrimidin-4-ylamino}-propionate

Produkt 1

HCID 866189272-Benzyloxycarbonylamino-3-{2-methoxy-5-methyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionic acid bis (trifluoroacetate)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

200 mg (0.317 mmole) of tert-butyl 2-benzyloxycarbonylamino-3-{2-methoxy-5-methyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionate in 10 ml of dichloromethane with 2 ml of trifluoroacetic acid is stirred at ambient temperature until the starting product disappears according to TLC (silica gel, eluent: CH2Cl2-MeOH—H2O—AcOH 90-10-1-1). Toluene is added and the reaction mixture is evaporated to dryness under reduced pressure (2 kPa). The residue is solubilized in the minimum amount of dichloromethane then poured into diisopropyl ether. 170 mg of expected product is obtained in the form of a beige solid.

Aufarbeitung

  1. customthe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  2. additionthen poured into diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c77bfc05b9df4c83bdec0a520551b88e
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765766B2

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