Triethylamine → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-dimethylaminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

HRID 394089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394089
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3Cl)[CH:15]=[C:16]([CH:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:33].[ClH:34].[CH3:35][NH:36][CH3:37].C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:17](=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[Cl:34])[CH:15]=[C:14]([CH:26]3[CH2:27][CH2:28][CH:29]([N:36]([CH3:37])[CH3:35])[CH2:30][CH2:31]3)[CH:13]=2)[CH2:12][NH:11][C:10]1=[O:33]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 226480091-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone2×

Produkt 1

HCID 226481491-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-dimethylaminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone (33 mg, 0.066 mmol) (INTERMEDIATE 73) in 1,2-dichloroethane (1.0 mL) at RT (under a nitrogen atmosphere) was added dimethylamine hydrochloride (11 mg, 0.132 mmol) followed by triethylamine (18 μL, 0.132 mmol). The reaction-mixture was stirred for 10 min then NaBH(OAc)3 (21 mg, 0.099 mmol) was added to the reaction. After 1.5 h the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution followed by brine, and dried over Na2SO4. The crude residue was purified by preparative thin layer chromatography using 5% MeOH in DCM as the eluent to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-dimethylaminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone (diastereomer A and diastereomer B).

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. customThe crude residue was purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-40c697062e00430396cc5dce43737223
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809199B2

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