Hydrochloric Acid → [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[3-(piperidin-4-yloxy)-phenyl]-amine

HRID 1262099Notes

Reaction equation

HRID 1262099 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[N:38]2[C:33]([CH:34]=[N:35][C:36](OS(C(F)(F)F)(=O)=O)=[N:37]2)=[CH:32][CH:31]=1.COCC(O)C.C(N(CC)C(C)C)(C)C.Cl>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[N:38]2[C:33]([CH:34]=[N:35][C:36]([NH:21][C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:16]=3)=[N:37]2)=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 57803194790667-68-4HCID 86661678Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66711727[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[3-(piperidin-4-yloxy)-phenyl]-amine

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(3-Amino-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (94 mg, 0.32 mmol), Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (100 mg, 0.3 mmol), 1-Methoxy-2-propanol (0.3 mL, 3 mmol), and N,N-Diisopropylethylamine (2 mL, 10 mmol) was heated and let stir overnight at 80° C. Concentrated added Hydrogen Chloride (2 mL, 60 mmol) and stir at room temperature for half and hour. The reaction was concentrated, dissolved in 2 mL DMSO, filtered and placed onto the Gilson. The pure fractions were frozen and lypholyzed over night to give [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[3-(piperidin-4-yloxy)-phenyl]-amine

Workup

  1. temperaturewas heated
  2. concentrationConcentrated
  3. stirringstir at room temperature for half and hour
  4. concentrationThe reaction was concentrated
  5. dissolutiondissolved in 2 mL DMSO
  6. filtrationfiltered
  7. temperatureThe pure fractions were frozen
  8. waitlypholyzed over night

Sources & evidence

ORD record
ord-1378713ab0c7484c9a682d84ac196df5
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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