HCID 23511825, Verbindung → methyl 4-[N-[1-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate

HRID 350397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350397
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:11].[N+:24]([C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[N:37]([CH2:39][CH:40]1[CH2:44][CH2:43][CH2:42][NH:41]1)[CH3:38])[C:30]([O:32][CH3:33])=[O:31])([O-:26])=[O:25]>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOCC.C1C=CC2N(O)N=NC=2C=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:41]2[CH2:42][CH2:43][CH2:44][CH:40]2[CH2:39][N:37]([C:36]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=2[N+:24]([O-:26])=[O:25])[CH3:38])=[O:23])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:11]

Komponenten

7

Edukt 2

HCID 23511825HCID 23511825, VerbindungHCID 23511932methyl 3-nitro-4-[N-(2-pyrrolidinyl)methyl-N-methylamino]benzoate

Produkt 1

HCID 69332166methyl 4-[N-[1-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoateAusbeute 105,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 757711-HydroxybenzotriazoleKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetic acid (630.0 mg, 1.979 mmol), methyl 3-nitro-4-[N-(2-pyrrolidinyl)methyl-N-methylamino]benzoate (553.0 mg, 1.885 mmol), EDC(Hydrochloride) (542.0 mg, 2.827 mmol), HOBt (25.5 mg, 0.189 mmol), and DMAP (23.1 mg, 0.189 mmol) in DMF (5.0 mL) was stirred at room temp. for 2 hr. The mixture was diluted with Et2O, washed with brine, and dried over Na2SO4. The solvent was removed under a reduced pressure, and the residue was chromatographed on silica-gel with CHCl3-MeOH (30:1, v/v) as eluent to afford 1.18 g (100%) methyl 4-[N-[1-[3-methoxy4-[N′-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate as a yellow foam, which is used to the subsequent reaction without further purification.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under a reduced pressure
  4. customthe residue was chromatographed on silica-gel with CHCl3-MeOH (30:1

Quellen und Nachweise

ORD-Eintrag
ord-fb623a385acd471e8992840f936a25a5
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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