Cyanuric chloride → HCID 57928429, compound

HRID 1360196Notes

Reaction equation

HRID 1360196 reaction equation
[O:1]=[C:2]1[N:13]([CH:14]2[CH:21]3[CH2:22][C:17]4([C:24]([NH2:26])=O)[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)[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.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:1]=[C:2]1[N:13]([CH:14]2[CH:21]3[CH2:22][C:17]4([C:24]#[N:26])[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)[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 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 57928357HCID 57928357, compound

Product 1

HCID 57928429HCID 57928429, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(2H)-yl)adamantan-1-carboxamide (70 mg) was suspended in N,N-dimethylformamide (1 ml), and 2,4,6-trichloro-1,3,5-triazine (37 mg) was added under ice cooling. The mixture was stirred at ambient temperature for 4 hours. To the reaction solution was added saturated aqueous sodium hydrogencarbonate, and the obtained solid was collected by filtration, washed with water and ethyl acetate to obtain 4-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(2H)-yl)adamantan-1-carbonitrile (30 mg).

Workup

  1. filtrationthe obtained solid was collected by filtration
  2. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-164bd3b114ce48b0b6f7b44310b5d2dd
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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