Acetonitrile → HCID 57444060, compound

HRID 1482473Notes

Reaction equation

HRID 1482473 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2=NN(N)[N:10]=[C:4]2[N:3]=1.CC[N:14]([CH2:17]C)CC.[C:19](Cl)(=[O:21])[CH3:20].CC#[N:25]>>[Br:1][C:2]1[N:3]2[N:25]=[C:17]([NH:14][C:19](=[O:21])[CH3:20])[N:10]=[C:4]2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6367Acetyl chlorideHCID 8471Triethylamine2×HCID 86638664HCID 86638664, compound

Product 1

HCID 57444060HCID 57444060, compound

Procedure

To a solution of the 5-bromo-2-amino-triazolopyridine (1 eq.) in dry CH3CN at 5° C. is added Et3N (2.5 eq.) followed by acetyl chloride (2.5 eq.). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material is consumed. If required, further Et3N (1 eq.) and acid chloride (1 eq.) are added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution and stirred at ambient temp. (for 16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by addition of water and extraction with ethyl acetate. The organic phase is then dried over MgSO4, evaporated in vacuo. The compound may be used without further purification.

Workup

  1. customis consumed
  2. customreaction
  3. customFollowing solvent evaporation in vacuo the resultant residue
  4. additionis treated with 7 N methanolic ammonia solution
  5. stirringstirred at ambient temp. (for 16 h)
  6. customProduct isolation is made by removal of volatiles in vacuo
  7. additionfollowed by addition of water and extraction with ethyl acetate
  8. dry with materialThe organic phase is then dried over MgSO4
  9. customevaporated in vacuo
  10. customThe compound may be used without further purification

Sources & evidence

ORD record
ord-01ac6efb5797441982bc0d9b91e83aea
Source dataset
uspto-grants-2016_08
Patent number
US09415037B2

Reaction notes

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