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

HRID 927234Notes

Reaction equation

HRID 927234 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH:15]([CH3:19])[C:16]([OH:18])=O)[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].C(N(CC)CC)C.F[B-](F)(F)F.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.[CH2:64]([CH2:66][NH2:67])[OH:65]>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH:15]([CH3:19])[C:16]([NH:67][CH2:66][CH2:64][OH:65])=[O:18])[C:13](=[O:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[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]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 903110912-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoic acid2×

Product 1

HCID 903114262-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)-N-(2-hydroxyethyl)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoic acid (intermediate 28, 40 mg, 85 μmol) and triethylamine (45 μL, 0.32 mmol) in N,N-dimethylformamide (1.5 mL) is treated with N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (27 mg, 85 μmol) and stirred at room temperature for 15 min Ethanolamine (12 μL, 0.21 mmol) is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with N,N-dimethylformamide and purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 37 mg; ESI mass spectrum [M+H]+=513; Retention time HPLC: 0.81 min (Z018_S04).

Workup

  1. additionis added
  2. custompurified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  3. custom0.81 min (Z018_S04)

Sources & evidence

ORD record
ord-43132bd2a0564e55a19c4955713a8013
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

Loading…