Cyanuric chloride → HCID 67277576, compound

HRID 1696260Notes

Reaction equation

HRID 1696260 reaction equation
[O:1]=[C:2]1[N:13]([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[C:20]([NH2:22])=O)[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3]1.ClC1N=C(Cl)N=C(Cl)N=1>CN(C)C=O.O>[O:1]=[C:2]1[N:13]([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[C:20]#[N:22])[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3]1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 67277939HCID 67277939, compound

Product 1

HCID 67277576HCID 67277576, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of rel-(1R,2S)-2-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)cyclohexanecarboxamide (14 mg) in N,N-dimethylformamide (140 μl) was added 2,4,6-trichloro-1,3,5-triazine (8.63 mg) at 0° C. The reaction mixture was stirred at ambient temperature overnight. The solution was diluted with water and extracted with EtOAc/tetrahydrofuran. The organic layer was dried over MgSO4 and concentrated in vacuo. The residual solid was washed with diisopropylethylether to give rel-(1R,2S)-2-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)cyclohexanecarbo-nitrile (3 mg) as a pale brown solid.

Workup

  1. extractionextracted with EtOAc/tetrahydrofuran
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. washThe residual solid was washed with diisopropylethylether

Sources & evidence

ORD record
ord-8c49ffdfcb004b56accbeb56001103c4
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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