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

HRID 59658Notes

Reaction equation

HRID 59658 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[O:12]=[C:13]1[NH:22][CH:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[S:31][CH3:32])[C:20]2[C:19](=[O:33])[CH2:18][CH2:17][CH2:16][C:15]=2[N:14]1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=1>ClCCl>[O:12]=[C:13]1[NH:22][CH:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[S:31]([CH3:32])=[O:6])[C:20]2[C:19](=[O:33])[CH2:18][CH2:17][CH2:16][C:15]=2[N:14]1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1186929024-[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 1186929064-[2,5-Dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-3-methanesulfinyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloroperoxybenzoic acid (77%, 111 mg, 0.495 mmol) is added at room temperature to a solution of 4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-3-methylsulfanyl-benzonitrile (INTERMEDIATE 6, 340 mg, purity 70%, 0.520 mmol) in dichloromethane (2 mL) and the mixture is stirred for 10 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-145b18da731a4e32980f3ebd175266f9
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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