4-Chloro-N-methylbenzenamine → 2-{2-[(4-Chlorophenyl)methyl carbamoyl]quinolin-6-yl}-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl Ester

HRID 1788591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788591
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[C:26]([C:31](O)=[O:32])[CH:25]=[CH:24]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH2:35][N:36](C(C)C)C(C)C.[Cl:43][C:44]1[CH:51]=[CH:50][C:47](NC)=[CH:46][CH:45]=1>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:19]([O:18][C:16]([C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]=[C:26]([C:31](=[O:32])[NH:36][CH2:35][C:47]3[CH:46]=[CH:45][C:44]([Cl:43])=[CH:51][CH:50]=3)[CH:25]=[CH:24]4)=[N:9][C:10]=2[CH:15]=1)=[O:17])[CH3:20]

Komponenten

6

Edukt 3

HCID 702724-Chloro-N-methylbenzenamineHCID 81531DiisopropylethylamineHCID 576029956-(1-Cyclohexyl-5-ethoxycarbonyl-1H-benzimidazol-2-yl)quinoline-2-carboxylic Acid

Produkt 1

HCID 689223652-{2-[(4-Chlorophenyl)methyl carbamoyl]quinolin-6-yl}-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl EsterAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 100 mg (0.23 mmol) Compound 402a in 1 mL SOCl2 was allowed to stand at room temperature for 10 min and SOCl2 was removed. The residue was dissolved in 5 mL anhydrous CH2Cl2; 89 mg (0.69 mmol) DIEA, 84 mg (0.69 mmol) DMAP, 98 mg (0.69 mmol) 4-chloro-N-methylaniline were added; and the solution was vortexed and allowed to stand at room temperature overnight. The solvent was removed and the residue was chromatographed on silica gel using hexane/EtOAc as the eluent to yield 63 mg of yellow oil. MS: 576.24 (M+H+).

Aufarbeitung

  1. customSOCl2 was removed
  2. dissolutionThe residue was dissolved in 5 mL anhydrous CH2Cl2
  3. waitto stand at room temperature overnight
  4. customThe solvent was removed
  5. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-93f36f4283284a6bb8c6a986ff4ff83f
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511145B2

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