2-(Methylamino)ethanol → 2-(4-(4-Cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)-N-(2-hydroxyethyl)-N-methyl-acetamide

HRID 927235Notes

Reaction equation

HRID 927235 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]([OH:18])=O)[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11]3[CH2:30][CH2:31][C:32](=[O:33])[C:10]2=3)=[C:5]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:4]=1)#[N:2].C(N(CC)CC)C.[CH3:45][NH:46][CH2:47][CH2:48][OH:49]>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]([N:46]([CH2:47][CH2:48][OH:49])[CH3:45])=[O:18])[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11]3[CH2:30][CH2:31][C:32](=[O:33])[C:10]2=3)=[C:5]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 903109962-(4-(4-Cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

Product 1

HCID 903111152-(4-(4-Cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)-N-(2-hydroxyethyl)-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-(4-cyano-2-(methylsulfonyl)phenyl)-2,5-dioxo-1-(3-(trifluoromethyl)-phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid (example 19, 23 mg, 43 μmol) and triethylamine (18 μL, 0.13 mmol) in N,N-dimethylformamide (1.0 mL) is stirred at room temperature for 5 min and treated with N,N,N′,N′-tetramethyl-0-(benzotriazol-1-yl)uronium tetrafluoroborate (13 mg, 43 μmol). After 5 min, 2-(methyl-amino)ethanol (10 μL, 0.13 mmol) is added. The mixture is stirred at room temperature for 3 h and purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 15 mg; ESI mass spectrum [M+H]+=591; Retention time HPLC: 0.89 min (Z011_S03).

Workup

  1. custompurified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom0.89 min (Z011_S03)

Sources & evidence

ORD record
ord-5226ac5970c540359f1ab799577f4fe9
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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