1,1'-Carbonyldiimidazole → HCID 178446207, compound

HRID 1672360Notes

Reaction equation

HRID 1672360 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([NH2:14])=[CH:4][CH:3]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:20]([OH:21])=[N:14][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57900557HCID 57900557, compound

Product 1

HCID 178446207HCID 178446207, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-N2-(pentan-3-yl)pyridine-2,3-diamine (936 mg, 4.37 mmol) in THF (10 mL) and CDI (1.1 g, 12.9 mmol) was added as a solid. After heating for 3 h, the reaction was cooled to room temperature. The excess CDI was quenched by the careful addition of water. The mixture was diluted with EtOAc and washed three times with water and once with brine. The solution was then dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (5%-40% EtOAc/hexanes) provided the title compound as a light purple solid (682 mg, 65%). m/z=240.0 (M+H)+

Workup

  1. temperatureAfter heating for 3 h
  2. customThe excess CDI was quenched by the careful addition of water
  3. additionThe mixture was diluted with EtOAc
  4. washwashed three times with water
  5. dry with materialThe solution was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b121dfd96ca4702a9852f97571008a7
Source dataset
uspto-grants-2011_08
Patent number
US07998976B2

Reaction notes

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