Pyridine → HCID 68753207, compound

HRID 624163Notes

Reaction equation

HRID 624163 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[CH:14]=[CH:15][CH:16]=[C:12]3[C:11](=[O:17])[NH:10][N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24]1([O:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[C:24]1([O:30][C:31](=[O:32])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:13]4[CH:14]=[CH:15][CH:16]=[C:12]4[C:11](=[O:17])[NH:10][N:9]=3)=[CH:6][CH:7]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 68749227HCID 68749227, compound

Product 1

HCID 68753207HCID 68753207, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 50 mg 4-(4-aminophenyl)pyrrolo[1,2-d][1,2,4]triazin-1(2H)-one (0.22 mmol) in 1 ml tetrahydrofuran at room temperature a solution of 0.03 ml pyridine (0.3 mmol) in 0.5 ml of tetrahydrofuran was added over 5 minutes. Subsequently, 0.03 ml phenylchlorformate (0.23 mmol) dissolved in 3 ml of tetrahydrofuran was added over 30 minutes and the reaction was stirred at room temperature overnight. The solvent was evaporated on vacuo and the mixture was directly incorporated on silica by dichloromethane. The mixture was purified by silica gel chromatography (4 g, cyclohexane:ethylacetate gradient) to afford crude material which was purified by column chromatography (cyclohexane:ethylacetate gradient) to afford the title compound.

Workup

  1. additionwas added over 5 minutes
  2. additionwas added over 30 minutes
  3. customThe solvent was evaporated on vacuo
  4. customThe mixture was purified by silica gel chromatography (4 g, cyclohexane:ethylacetate gradient)
  5. customto afford crude material which
  6. customwas purified by column chromatography (cyclohexane:ethylacetate gradient)

Sources & evidence

ORD record
ord-4251f16dcda9466d86d53594b2a1ca08
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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