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

HRID 394089Notes

Reaction equation

HRID 394089 reaction equation
[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]

Participants

7

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-40c697062e00430396cc5dce43737223
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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