Ammonia → HCID 59515624, compound

HRID 1160174Notes

Reaction equation

HRID 1160174 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 21%

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, 21%).

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-2b483ed9056d4ed39cef9a71c84b1f75
Source dataset
uspto-grants-2010_10
Patent number
US07816369B2

Reaction notes

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