Triethylamine → [1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl-methyl]-carbamic acid tert-butyl ester

HRID 2416848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2416848
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14](Cl)=[C:15]([F:20])[CH:16]=2)[N:11]([CH:22]2[CH2:24][CH2:23]2)[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:30][C:31](=[O:39])[N:32](C1CCNC1)[CH3:33])([CH3:29])([CH3:28])[CH3:27].C([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C>CN(C=O)C.O>[C:26]([O:30][C:31](=[O:39])[NH:32][CH2:33][CH:46]1[CH2:44][CH2:43][N:42]([C:14]2[CH:13]=[C:12]3[C:17]([C:18](=[O:19])[N:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:10](=[O:25])[N:11]3[CH:22]3[CH2:24][CH2:23]3)=[CH:16][C:15]=2[F:20])[CH2:45]1)([CH3:29])([CH3:28])[CH3:27]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidineHCID 226328893-Benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione

Produkt 1

HCID 53711025[1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl-methyl]-carbamic acid tert-butyl esterAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 3-benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione (Example E-3, 0.162 g, 0.44 mmol) in DMF (3.0 mL) was reacted with pyrrolidin-3-yl-methyl-carbamic acid tert-butyl ester (0.40 g, 2.0 mmol) and triethylamine (0.63 mL, 4.5 mmol) then heated to 70° C. for 2 days. The mixture was then cooled, diluted with H2O, and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 0.127 g of the title compound as a solid.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-af14b42b39e8432fb74783d33c2283ef
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825199B2

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