m-Chloroperbenzoic acid → 3-Methanesulfinyl-4-[3-methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

HRID 59659Notes

Reaction equation

HRID 59659 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][N:13]1[CH:22]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[S:31][CH3:32])[C:21]2[C:20](=[O:33])[CH2:19][CH2:18][CH2:17][C:16]=2[N:15]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=2)[C:14]1=[O:44]>ClCCl>[CH3:32][S:31]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:23]=1[CH:22]1[C:21]2[C:20](=[O:33])[CH2:19][CH2:18][CH2:17][C:16]=2[N:15]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:43])[F:41])[CH:35]=2)[C:14](=[O:44])[N:13]1[CH3:12])[C:27]#[N:28])=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1186929224-[3-Methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-3-methylsulfanyl-benzonitrile2×

Product 1

HCID 1186928953-Methanesulfinyl-4-[3-methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloroperoxybenzoic acid (77%, 15.3 mg, 0.068 mmol) is added at room temperature to a solution of 4-[3-methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-3-methylsulfanyl-benzonitrile (INTERMEDIATE 7, 41 mg, 0.076 mmol) in dichloromethane (1 mL), and the mixture is stirred for 40 min. The reaction mixture is concentrated under reduced pressure and purified by reversed phase HPLC (X-Bridge C18, gradient of acetonitrile in water, 0.1% NH4OH) yielding the two diasteromers of the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompurified by reversed phase HPLC (X-Bridge C18, gradient of acetonitrile in water, 0.1% NH4OH)

Sources & evidence

ORD record
ord-d85183a82d2543529fad38f898cc6d36
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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