Cyclopropylamine → N5-cyclopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine

HRID 2382774Notes

Reaction equation

HRID 2382774 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.C(N(C(C)C)C(C)C)C>C(O)CCC>[CH:16]1([NH:19][C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 252161845-Chloro-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 59437445N5-cyclopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamineYield 51.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 5-chloro-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A7), 3.60 g; 15.22 mmol; 1.0 eq.), cyclopropylamine (5.27 mL; 76.1 mmol; 5.0 eq.), and N-ethyldiisopropylamine (26.22 mL; 152.2 mmol; 10.0 eq.) was heated at 80° C. in 1-butanol (36.0 mL) for 23 h., then 15 h. at 100° C. The reaction mixture was then concentrated under vacuum till dryness. Diethyl ether was added and the solid was filtered, washed with water and dried. The product was then purified by chromatography on silicagel (from 5% to 95% EtOAc in c-Hex), to give the title compound as a white solid (2.0 g; 51.1%). HPLC, Rt: 2.54 min. (purity 100%). LC/MS, M+(ESI): 258.0, M−(ESI): 256.0.

Workup

  1. custom15 h.
  2. customat 100° C
  3. concentrationThe reaction mixture was then concentrated under vacuum till dryness
  4. additionDiethyl ether was added
  5. filtrationthe solid was filtered
  6. washwashed with water
  7. customdried
  8. customThe product was then purified by chromatography on silicagel (from 5% to 95% EtOAc in c-Hex)

Sources & evidence

ORD record
ord-c01dd4be239145a3acb93bf64da15100
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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