Ethanesulfonyl chloride → 4-(3-(Ethylsulfonyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile

HRID 927248Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([S:15]([CH2:18][CH2:19]CC(OC)=O)(=[O:17])=[O:16])[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:11]3[CH2:36][CH2:37][C:38](=[O:39])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2].C(S(Cl)(=O)=O)C>>[CH2:18]([S:15]([N:14]1[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[C:10]2[C:38](=[O:39])[CH2:37][CH2:36][C:11]=2[N:12]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)[C:13]1=[O:25])(=[O:16])=[O:17])[CH3:19]

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 90310908Methyl 4-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-ylsulfonyl)butanoate

Product 1

HCID 903115814-(3-(Ethylsulfonyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile

Procedure

The title compound is prepared in analogy to methyl 4-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl-sulfonyl)butanoate (example 34), substituting 4-(chlorosulfonyl)butanoate with ethane-sulfonyl chloride. Yield: 11 mg; ESI mass spectrum [M+H]+=490; Retention time HPLC: 0.94 min (Z018_S04).

Workup

custom0.94 min (Z018_S04)

Sources & evidence

ORD record: ord-6ac833ff69814af28e571b61ca7935ef
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290459B1

Reaction notes

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