1,2-Dichloroethane → methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate

HRID 354494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354494
[CH3:1][NH:2][CH2:3][C:4]([CH3:17])([O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH3:5].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](O)=[O:36])=[CH:30][C:29]=1[O:38][CH3:39].C(Cl)CCl.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([CH2:1][NH:2][CH2:3][C:4]([CH3:17])([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH3:5])=[O:36])=[CH:30][C:29]=1[O:38][CH3:39]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 23511825HCID 23511825, VerbindungHCID 69333050Methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate

Produkt 1

HCID 69334761methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoateAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate (200 mg, 0.84 mmol), 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetic acid (268 mg, 0.84 mmol), 4-DMAP (125 mg, 1.0 mmol) in DMF (5 mL) was added EDC (220 mg, 1.14 mmol) at ambient temp. The resulting mixture was stirred for a further 10 hr at ambient temp. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated. The residual gum was triturated with CH2Cl2 and Et2O to give 200 mg (44.1%) methyl 4-[[1-[4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate as a crystalline material. 1H-NMR (CDCl3) δ1.36 and 1.31 (each s, 6H), 3.24-3.88 (series of s, 13 H), 6.65-8.20 (series of m, 14H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residual gum was triturated with CH2Cl2 and Et2O

Quellen und Nachweise

ORD-Eintrag
ord-a2935f98208d4f0290ee014926308275
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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