2-Propanol, 1-amino-2-methyl- → 4-(4-Cyanophenyl)-N-(2-hydroxy-2-methylpropyl)-2,5-dioxo-1-(2-(trifluoromethyl)-pyridin-4-yl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide

HRID 927259Notes

Reaction equation

HRID 927259 reaction equation
C(C1C=CC(C2N(C(NC)=O)C(=O)N(C3C=CC=C(C(F)(F)F)C=3)C3CCC(=O)C2=3)=C(F)C=1)#N.[C:35]([C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[N:48]([C:49](OC3C=CC([N+]([O-])=O)=CC=3)=[O:50])[C:47](=[O:61])[N:46]([C:62]3[CH:67]=[CH:66][N:65]=[C:64]([C:68]([F:71])([F:70])[F:69])[CH:63]=3)[C:45]3[CH2:72][CH2:73][C:74](=[O:75])[C:44]2=3)=[CH:39][CH:38]=1)#[N:36].[NH2:76][CH2:77][C:78]([CH3:81])([OH:80])[CH3:79]>>[C:35]([C:37]1[CH:38]=[CH:39][C:40]([CH:43]2[N:48]([C:49]([NH:76][CH2:77][C:78]([OH:80])([CH3:81])[CH3:79])=[O:50])[C:47](=[O:61])[N:46]([C:62]3[CH:67]=[CH:66][N:65]=[C:64]([C:68]([F:71])([F:70])[F:69])[CH:63]=3)[C:45]3[CH2:72][CH2:73][C:74](=[O:75])[C:44]2=3)=[CH:41][CH:42]=1)#[N:36]

Participants

4

Reactant 3

HCID 951022-Propanol, 1-amino-2-methyl-HCID 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 903109874-nitrophenyl 4-(4-cyanophenyl)-2,5-dioxo-1-(2-(trifluoromethyl)pyridin-4-yl)-4,5, 6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxylate2×

Product 1

HCID 903110114-(4-Cyanophenyl)-N-(2-hydroxy-2-methylpropyl)-2,5-dioxo-1-(2-(trifluoromethyl)-pyridin-4-yl)-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-nitrophenyl 4-(4-cyanophenyl)-2,5-dioxo-1-(2-(tri-fluoromethyl)pyridin-4-yl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxylate (intermediate 30.3, 100 mg, 0.25 mmol) as starting material and employing 1-amino-2-methylpropan-2-ol as reagent. Yield: 60 mg; ESI mass spectrum [M+H]+=514; Retention time HPLC: 0.97 min (Z018_S04).

Workup

  1. custom0.97 min (Z018_S04)

Sources & evidence

ORD record
ord-798fc14da93b4a7a9d36f7697a812e7c
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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