Methyl chloroformate → (S)-Methyl 4-(4-cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxylate

HRID 927246Notes

Reaction equation

HRID 927246 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([C:15]([O:17][CH2:18]C)=[O:16])[C:13](=[O:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11]3[CH2:31][CH2:32][C:33](=[O:34])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2].O=C1N(C2C=CC=C(C(F)(F)F)C=2)C2CCC(=O)C=2[C@@H](C2C=CC(C#N)=C[C:57]=2[S:64](C)(=[O:66])=[O:65])N1.ClC(OC)=O>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[N:14]([C:15]([O:17][CH3:18])=[O:16])[C:13](=[O:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11]3[CH2:31][CH2:32][C:33](=[O:34])[C:10]2=3)=[C:5]([S:64]([CH3:57])(=[O:66])=[O:65])[CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 77844826(S)-4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)-3-(methylsulfonyl)benzonitrileHCID 90311087Ethyl 4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxylate

Product 1

HCID 90326505(S)-Methyl 4-(4-cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxylate

Procedure

The title compound is prepared in analogy to ethyl 4-(4-cyanophenyl)-2,5-dioxo-1-(3-(tri-fluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxylate (example 31, 110 mg, 0.23 mmol), using (S)-4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methylsulfonyl)benzonitrile (example 10A) as starting material and substituting ethyl chloroformate with methyl chloroformate. Yield: 76 mg; ESI mass spectrum [M+H]+=534; Retention time HPLC: 1.01 min (Z018_S04).

Workup

  1. custom1.01 min (Z018_S04)

Sources & evidence

ORD record
ord-e7529d33da774b07a2a2a40ea60e114f
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

Loading…