Ammonia → HCID 59515624, compound

HRID 2409254Notes

Reaction equation

HRID 2409254 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[NH3:18]>C(O)C>[NH:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:3]1[N:4]=[C:5]([NH2:18])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 24214652HCID 24214652, compound

Product 1

HCID 59515624HCID 59515624, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3,6-Dichloro-pyridin-2-yl)-1H-benzoimidazole (20 mg; 0.076 mmol) was dissolved in ethanol (1.5 ml) and concentrated ammonia (2 ml) in a pressure tube. After 1000 minutes in a microwave at 140° C. and 200 psi, the solvents were removed and the residue dissolved in isopropyl alcohol (1 ml) and concentrated ammonia (1 ml) before microwaving as before. The solvents were evaporated and the residue chromatographed on silica gel with 80% ethyl acetate in heptane to give 6-(1H-benzoimidazol-2-yl)-5-chloro-pyridin-2-ylamine (4 mg, 2.1%).

Workup

  1. custom200 psi, the solvents were removed
  2. dissolutionthe residue dissolved in isopropyl alcohol (1 ml)
  3. customconcentrated ammonia (1 ml) before microwaving as before
  4. customThe solvents were evaporated
  5. customthe residue chromatographed on silica gel with 80% ethyl acetate in heptane

Sources & evidence

ORD record
ord-cb197dbbcda74efc876ccc170dbb967d
Source dataset
uspto-grants-2014_08
Patent number
US08815895B2

Reaction notes

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