2-Chloropyrimidine → HCID 10382599, compound

HRID 1270155Notes

Reaction equation

HRID 1270155 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]2[N:7]([C:16](=[O:19])[NH:17][N:18]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([F:15])[CH:9]=2.Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O>[F:15][C:10]1[CH:9]=[C:8]2[C:13]([N:14]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:6]3[N:7]2[C:16](=[O:19])[NH:17][N:18]=3)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 744042-Chloropyrimidine2×HCID 81531DiisopropylethylamineHCID 18449173HCID 18449173, compound

Product 1

HCID 10382599HCID 10382599, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 50 mg of 4-(2-amino-ethylamino)-8-fluoro-2H-[1,2,4]triazolo[4,3-a]quinoxalin-1-one 13.5 mg of 2-chloropyrimidine, and 76 mg of diisopropylethylamine in DMSO (0.5 mL) was heated for 18 hrs. An additional 13.5 mg of 2-chloropyrimidine was added and heating was continued for another 18 hrs. The reaction was diluted with EtOAc, washed with water, and dried over sodium sulfate prior to concentration. The residue was separated by silica gel chromatography, and the isolated residue was recrystallized from MeOH to give the title compound. MS (M−H)−=339.0.

Workup

  1. temperaturewas heated for 18 hrs
  2. temperatureheating
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationto concentration
  6. customThe residue was separated by silica gel chromatography
  7. customthe isolated residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-804ea7f139e44251a56c40c5455dab58
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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