Methyl 4-chloroanthranilate → 3-Benzyl-7-chloro-1-pyrrolidine-2-yl-2,3-dihydro-1H-quinazoline-4-one

HRID 225768

Reaktionsgleichung

Reaktionsgleichung von HRID 225768
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1C(O)=O)=O)(C)(C)C.CO[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[NH2:26].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C([N:55]([CH:58]([CH3:60])C)[CH2:56]C)(C)C.C(OC(N1[CH2:72][CH2:71][CH2:70][CH:69]1[C:73](=O)NC1C=C(Cl)C=CC=1C(OC)=O)=O)(C)(C)C>N1C=CC=CC=1>[CH2:58]([N:55]1[C:18](=[O:27])[C:19]2[C:20](=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[N:26]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH2:56]1)[C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:73]=1

Komponenten

7

Edukt 5

HCID 80001Methyl 4-chloroanthranilateHCID 81531DiisopropylethylamineHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 2733179PyBroPHCID 866092502-(5-Chloro-2-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 690643443-Benzyl-7-chloro-1-pyrrolidine-2-yl-2,3-dihydro-1H-quinazoline-4-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Formula 103 where T is a covalent bond: W, X, Y and Z are —C═: U′—V′ is —N(R6′)—CReRf—; R1, R2, R4, and Ra to Rf are H: R3 is chloro; and R6′ is Boc A solution of pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (6.0 g, 28 mmol), 2-amino-4-chloro-benzoic acid methyl ester (4.6 g, 25 mmol), PyBroP (14.4 g, 31 mmol), diisopropylethylamine (6 mL) in pyridine (60 mL) was stirred overnight at room temperature, after which HPLC/MS showed complete conversion of starting material. The solvents were removed under vacuum and the residue partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was washed with 1M HCl (50 mL) and saturated NaHCO3 (50 mL), dried over MgSO4, filtered, and concentrated under vacuum. Silica gel chromatography using 30% ethyl acetate/hexanes as eluent gave 9.3 g (87% yield) of the desired product of Formula 103, 2-(5-chloro-2-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, as a yellow foam. LRMS (MH+) m/z 383.

Aufarbeitung

  1. customThe solvents were removed under vacuum
  2. customthe residue partitioned between ethyl acetate (100 mL) and water (50 mL)
  3. washThe organic layer was washed with 1M HCl (50 mL) and saturated NaHCO3 (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dfdffe169ecb4bd9a73d4f3be2914829
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557115B2

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