Ammonia → 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetamide

HRID 927218Notes

Reaction equation

HRID 927218 reaction equation
F[B-](F)(F)F.C[N+:7](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[N:36]([CH2:37][C:38](O)=[O:39])[C:35](=[O:41])[N:34]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:51])([F:50])[F:49])[CH:43]=3)[C:33]3[CH2:52][CH2:53][C:54](=[O:55])[C:32]2=3)=[CH:27][CH:26]=1)#[N:24].C(N(CC)C(C)C)(C)C.N>CN(C)C=O>[C:23]([C:25]1[CH:26]=[CH:27][C:28]([CH:31]2[N:36]([CH2:37][C:38]([NH2:7])=[O:39])[C:35](=[O:41])[N:34]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:49])([F:51])[F:50])[CH:43]=3)[C:33]3[CH2:52][CH2:53][C:54](=[O:55])[C:32]2=3)=[CH:29][CH:30]=1)#[N:24]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 903109622-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

Product 1

HCID 903109542-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (43 mg, 0.13 mmol) is added to a solution of 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoro-methyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid (example 4, 60 mg, 0.13 mmol) and N,N-diisopropylethylamine (50 μL, 0.29 mmol) in N,N-dimethylformamide (0.5 mL). After 20 min aqueous ammonia (32%, 8 μL, 0.13 mmol) added and the mixture is stirred at room temperature for 1 h. The mixture is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 36 mg; ESI mass spectrum [M+H]+=455; Retention time HPLC: 0.50 min (X012_S01).

Workup

  1. customThe mixture is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  2. custom0.50 min (X012_S01)

Sources & evidence

ORD record
ord-8e91f5b28ade41bdb884da82db4da5c8
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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