Potassium Carbonate → 4-(3-(2-(Methylsulfonyl)ethyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

HRID 517248Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][S:10]([CH3:13])(=[O:12])=[O:11].[O:14]=[C:15]1[NH:24][CH:23]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[C:22]2[C:21](=[O:33])[CH2:20][CH2:19][CH2:18][C:17]=2[N:16]1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=1>CN(C)C=O>[CH3:13][S:10]([CH2:9][CH2:8][N:24]1[CH:23]([C:25]2[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[CH:31][CH:32]=2)[C:22]2[C:21](=[O:33])[CH2:20][CH2:19][CH2:18][C:17]=2[N:16]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:41])[F:42])[CH:35]=2)[C:15]1=[O:14])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

Potassium carbonate (67 mg, 0.486 mmol) and 1-bromo-2-(methylsulfonyl)ethane (68 mg, 0.365 mmol) are added to a solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile (example 1, 100 mg, 0.243 mmol) in N,N-dimethylformamide (3 mL). The mixture is heated at 50° C. for 3 d and then purified by reversed phase HPLC (first purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3; second purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 22 mg; ESI mass spectrum [M+H]+=518; Retention time HPLC: 0.86 min (Z011_S03).

Workup

custompurified by reversed phase HPLC (first purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3; second purification: Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
custom0.86 min (Z011_S03)

Sources & evidence

ORD record: ord-bdf6826932084b249438b8eff81b5e93
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115093B2

Reaction notes

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