Ammonia → HCID 71293382, compound

HRID 921046Notes

Reaction equation

HRID 921046 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[NH:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.N.O1CCOC[CH2:19]1>>[CH:6]1[C:7]2[C:8]3[N:9]([CH:19]=[N:1][C:2]=2[N:3]=[CH:4][CH:5]=1)[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[N:12]=3

Participants

4

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 135214193-(1H-Benzimidazol-2-yl)pyridin-2-amine

Product 1

HCID 71293382HCID 71293382, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 100 mmol of the 2-(2-aminopyridin-3-yl)benzimidazole derivative (employed as equimolar mixture with the corresponding 2-tert-butylbenzimidazole derivative as obtained from synthesis 16)) and 1 mol of the corresponding carboxylic acid chloride is heated for 8 to 40 h under reflux in the case of carboxylic acid chlorides which boil below 150° C. or at 150° C. to 180° C. in the case of carboxylic acid chlorides which boil above 150° C., until the 2-(2-aminopyridin-3-yl)benzimidazole derivative has reacted. The reaction mixture is allowed to cool to 80° C., optionally diluted with 100 ml of dioxane, then stirred into a mixture of 500 ml of conc. ammonia solution and 500 g of ice and stirred for a further 3 h. The solid is subsequently filtered off with suction, washed twice with 100 ml of water in each case and dried in vacuo. The solid is taken up in 1000 ml of ethyl acetate, filtered through a short silica-gel column, rinsed with 500 ml of ethyl acetate, the ethylacetate is removed in vacuo, and the brown residue is recrystallised from methanol. The solids obtained in this way are freed from low-boiling components and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 170-200° C.). Purity according to 1H-NMR typically >99.5%.

Workup

  1. temperatureis heated for 8 to 40 h
  2. customhas reacted
  3. filtrationThe solid is subsequently filtered off with suction
  4. washwashed twice with 100 ml of water in each case
  5. customdried in vacuo
  6. filtrationfiltered through a short silica-gel column
  7. washrinsed with 500 ml of ethyl acetate
  8. customthe ethylacetate is removed in vacuo
  9. customthe brown residue is recrystallised from methanol
  10. customThe solids obtained in this way
  11. customare freed from low-boiling components and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 170-200° C.)

Sources & evidence

ORD record
ord-a23e167e54fd488282699fc744b7097e
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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