3-(Methylthio)propylamine → [6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-methylsulfanyl-propyl)-amine

HRID 1497809Notes

Reaction equation

HRID 1497809 reaction equation
[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:5]2[N:6]([N:8]=[C:9](Cl)[N:10]=2)[CH:7]=1.[CH3:23][S:24][CH2:25][CH2:26][CH2:27][NH2:28]>>[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:5]2[N:6]([N:8]=[C:9]([NH:28][CH2:27][CH2:26][CH2:25][S:24][CH3:23])[N:10]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 777433-(Methylthio)propylamine3×HCID 867081156-Bromo-2-chloro-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 86708116[6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-methylsulfanyl-propyl)-amine

Conditions

Temperature
155 °C

Procedure

To a suspension of 6-bromo-2-chloro-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (Int. 29, 125 mg, 0.32 mmol) in IMS (5 mL) was added 3-methylsulfanyl-propylamine (215 μL, 1.92 mmol) and the reaction mixture was heated under microwave irradiation at 155° C. for 2 hrs. After this time more 3-methylsulfanyl-propylamine (490 μL) was added and heating continued for 3 hrs then a further portion of 3-methylsulfanyl-propylamine (490 μL) was added and heating continued for 7 hrs. The resultant residue was loaded onto an SCX-2 cartridge and eluted with MeOH and then further purified by flash chromatography, eluting with a gradient of 0-50% EtOAc in cyclohexane to give the title compound as a colourless glass (57 mg).

Workup

  1. temperatureheating
  2. temperatureheating
  3. waitcontinued for 7 hrs
  4. washeluted with MeOH
  5. customfurther purified by flash chromatography
  6. washeluting with a gradient of 0-50% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-0f847b76b1654c3ba4e6ff3896c601bb
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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