Triethylamine → (2R,4S)-tert-Butyl 2-(dimethylcarbamoyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate

HRID 2189212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189212
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[N:15]=2)[CH2:10][C@@H:9]1[C:32]([OH:34])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:36][NH:37][CH3:38].[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.C(N(CC)CC)C>CN(C=O)C.O>[CH3:36][N:37]([CH3:38])[C:32]([C@H:9]1[CH2:10][C@H:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[N:15]=2)[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:34]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67366705(2R,4S)-1-(tert-Butoxycarbonyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-2-carboxylic acid

Produkt 1

HCID 67366947(2R,4S)-tert-Butyl 2-(dimethylcarbamoyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (2R,4S)-1-(tert-butoxycarbonyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-2-carboxylic acid (0.095 g, 0.204 mmol), dimethylamine hydrochloride (0.017 g, 0.204 mmol), 0-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.077 g, 0.204 mmol), and triethylamine (0.037 mL, 0.265 mmol) in DMF (1 mL) was stirred for 24 hours. Water (20 mL) was added and the aqueous layer was extracted with ethyl acetate (3×20 mL). The organic extracts were combined, dried (MgSO4) and concentrated. Purification by silica gel chromatography (10% methanol in dichloromethane) gave the title compound as a solid (0.090 g, 90%).

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-cf4c8a443031465dadbd2fc3034c041c
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324226B2

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