Hydrochloric Acid → HCID 10143150, Verbindung

HRID 2414826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414826
C(O[C:6](=[O:32])[NH:7][CH2:8][CH2:9][N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[CH:16]=2)[CH:11]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)(C)(C)C.Cl.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:46][C:47]1[C:56]2[C:51](=[N:52][C:53]([CH3:57])=[CH:54][CH:55]=2)[N:50]=[CH:49][CH:48]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CC(O)=O.O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH:11]2[C:12]3[C:17](=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[CH2:18][CH2:19][N:10]2[CH2:9][CH2:8][NH:7][C:6]([NH:46][C:47]2[C:56]3[C:51](=[N:52][C:53]([CH3:57])=[CH:54][CH:55]=3)[N:50]=[CH:49][CH:48]=2)=[O:32])=[CH:26][CH:27]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 2724254Sodium bis(trimethylsilyl)amideHCID 124552017-Methyl-[1,8]naphthyridin-4-ylamineHCID 69763736{2-[1-(4-fluoro-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 10143150HCID 10143150, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of {2-[1-(4-fluoro-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester (example 106.1, 0.22 g, 0.5 mmol) in glacial AcOH (1 mL) is added conc. HCl (0.1 mL). After 5 min, the reaction mixture is partitioned with CHCl3 (20 mL) and 1 N NaOH (15 mL). The organic phase is evaporated. The residue is taken up in DMSO (2 mL) and treated with CDI (0.2 g, 0.6 mmol, 1.2 eq). The reaction mixture is stirred at rt for 3 h, and then 4-amino-7-methyl-[1,8]-naphthyridine (example C5, 0.19 g, 0.6 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at rt for 30 min, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

Aufarbeitung

  1. customthe reaction mixture is partitioned with CHCl3 (20 mL) and 1 N NaOH (15 mL)
  2. customThe organic phase is evaporated
  3. stirringThe reaction mixture is stirred at rt for 30 min
  4. customThe reaction mixture is evaporated
  5. customthe residue purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0ff791c0f9cb4120988598d97de24975
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06815451B2

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