3-Amino-1-propanol → 4-(4-Cyanophenyl)-1-(3-(difluoromethyl)phenyl)-N-(3-hydroxypropyl)-2,5-dioxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide

HRID 927258Notes

Reaction equation

HRID 927258 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([C:15]([NH:17][CH3:18])=[O:16])[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])(F)[F:27])[CH:21]=3)[C:11]3[CH2:30][CH2:31][C:32](=[O:33])[C:10]2=3)=[C:5](F)[CH:4]=1)#[N:2].FC(F)C1C=C(N2C3C[CH2:50][C:51](=[O:52])C=3C(C3C=CC(C#N)=CC=3)NC2=O)C=CC=1.NCCCO>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([C:15]([NH:17][CH2:18][CH2:50][CH2:51][OH:52])=[O:16])[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([F:27])[F:29])[CH:21]=3)[C:11]3[CH2:30][CH2:31][C:32](=[O:33])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 90863-Amino-1-propanolHCID 903107184-(4-Cyano-2-fluorophenyl)-N-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamideHCID 903108234-(1-(3-(Difluoromethyl)phenyl)-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrile

Product 1

HCID 903108794-(4-Cyanophenyl)-1-(3-(difluoromethyl)phenyl)-N-(3-hydroxypropyl)-2,5-dioxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide

Procedure

The title compound is prepared in analogy to 4-(4-cyano-2-fluorophenyl)-N-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide (example 49), using 4-(1-(3-(difluoromethyl)phenyl)-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile (example 11, 100 mg, 0.26 mmol) as starting material and replacing methylamine with 3-aminopropanol. Yield: 70 mg; ESI mass spectrum [M+H]+=481; Retention time HPLC: 0.71 min (005_CA01).

Sources & evidence

ORD record
ord-ccec8465cf1b468bbb7804a22d1b1beb
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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