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

HRID 927215Notes

Reaction equation

HRID 927215 reaction equation
[CH3:1][N:2]1[CH:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[C:6]2[C:16](=[O:19])[CH2:17][CH2:18][C:5]=2[N:4]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C:3]1=[O:30].O=C1N(C2C=CC=C(C(F)(F)F)C=2)C2CCC(=O)C=2[C@@H](C2C=CC(C#N)=CC=2)N1>>[CH3:1][N:2]1[C@H:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[C:6]2[C:16](=[O:19])[CH2:17][CH2:18][C:5]=2[N:4]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=2)[C:3]1=[O:30]

Participants

3

Reactant 2

HCID 77844774(R)-4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrileHCID 903108904-(3-Methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile

Product 1

HCID 90310889(R)-4-(3-Methyl-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 4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile (example 2), using (R)-4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile (example 1A, 40 mg, 0.10 mmol) as starting material. Yield: 20 mg; ESI mass spectrum [M+H]+=412; Retention time HPLC: 0.59 min (X012_801).

Workup

  1. custom0.59 min (X012_801)

Sources & evidence

ORD record
ord-681d1586328141a5af5c0c48f63a39d2
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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