6-Methoxy-3-pyridinylamine → HCID 19890713, compound

HRID 893569Notes

Reaction equation

HRID 893569 reaction equation
[F:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[N:25][CH:26]=1>C(Cl)Cl>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:5]([C:2]2([F:1])[CH2:4][CH2:3]2)=[O:7])=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 811216-Methoxy-3-pyridinylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 97937151-Fluorocyclopropanecarboxylic acid

Product 1

HCID 19890713HCID 19890713, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Fluorocyclopropanecarboxylic acid (crude) (0.84 g, 0.0081 moles) was added in two portions to a solution of methylene chloride (50 ml ) and carbonyl di-imidazole (1.31 g, 0.0081 moles). The reaction was allowed to stand for 1 hour and then 5-amino-2-methoxypyridine (0.83 ml , 0.0081 moles) was added to it in one portion. The reaction mixture was allowed to stand at room temperature for 1 hour. The reaction mixture was then washed with saturated sodium bicarbonate (50 ml ), 5% hydrochloric acid (20 ml ) and saturated sodium bicarbonate solution (25 ml ); dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give 0.5 g of crude N-(2-methoxy-5-pyridyl)-1-fluorocyclopropanecarboxamide.

Workup

  1. waitto stand at room temperature for 1 hour
  2. washThe reaction mixture was then washed with saturated sodium bicarbonate (50 ml ), 5% hydrochloric acid (20 ml ) and saturated sodium bicarbonate solution (25 ml )
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-bdff6da268334128b7a5e017e2973d2b
Source dataset
uspto-grants-1992_06
Patent number
US05126338

Reaction notes

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