Potassium Carbonate → HCID 58312848, compound

HRID 1751187Notes

Reaction equation

HRID 1751187 reaction equation
[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[N:18]=[C:17](/[CH:19]=[C:20]4/[C:21](=[O:26])[NH:22][C:23](=[O:25])[S:24]/4)[CH:16]=[CH:15][N:14]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Br[CH2:29][C:30]([NH2:32])=[O:31].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:25]=[C:23]1[N:22]([CH2:29][C:30]([NH2:32])=[O:31])[C:21](=[O:26])/[C:20](=[CH:19]/[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([N:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:3]=[CH:2][C:1]([CH3:27])=[CH:6][CH:5]=4)[CH2:12][CH2:11]3)[N:18]=2)/[S:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 53251919HCID 53251919, compound

Product 1

HCID 58312848HCID 58312848, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To 10 mg of (Z)-5-((2-(4-(p-tolyl)piperazin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione was added 4 mg of 2-bromoacetamide, 4 mg of potassium carbonate, and 0.5 mL of DMF. The reaction mixture was heated to 55° C. for 4 h, concentrated under reduced pressure, and purified using reverse phase HPLC (MS-triggered fraction collection) with an acetonitrile/water gradient using trifluoroacetic acid as a modifier. The pure fractions were then concentrated under reduced pressure (Genevac HT-4) to provide (Z)-2-(2,4-dioxo-5-((2-(4-(p-tolyl)piperazin-1-yl)pyrimidin-4-yl)methylene)thiazolidin-3-yl)acetamide (4 mg, 11.5 mg theoretical, 35%). LC-MS m/z: 439 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified
  3. customphase HPLC (MS-triggered fraction collection) with an acetonitrile/water gradient
  4. concentrationThe pure fractions were then concentrated under reduced pressure (Genevac HT-4)

Sources & evidence

ORD record
ord-f062348bd32c40619482db30fbb43fd6
Source dataset
uspto-grants-2015_10
Patent number
US09157077B2

Reaction notes

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