Trifluoroacetic acid → HCID 178511731, compound

HRID 707223Notes

Reaction equation

HRID 707223 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:13]2[C:18]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=O)=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(O)(=O)C>[CH:22]1([C:20]2[N:12]([C@H:10]3[CH2:11][C@H:8]([NH2:7])[CH2:9]3)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:18]3[N:19]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454117HCID 178454117, compound

Product 1

HCID 178511731HCID 178511731, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

Tert-butyl(trans-3-((3-(cyclopropanecarboxamido)pyridin-2-yl)amino)cyclobutyl)carbamate (1.27 g, 3.67 mmol, was dissolved in acetic acid (300 mL) and heated at 105° C. After 4½ hours, trifluoroacetic acid (1 mL) was added and the reaction stirred at 105° C. After heating for an additional 5 hours, the reaction was evaporated to dryness under reduced pressure. The crude product was free based by partitioning between dichloromethane and saturated aqueous sodium bicarbonate. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was purified using silica chromatography (0-10% methanol in dichloromethane gradient) to give trans-3-(2-cyclopropyl-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutanamine (0.579 g, 2.54 mmol, 53.9% yield).

Workup

  1. waitAfter 4½ hours
  2. temperatureAfter heating for an additional 5 hours
  3. customthe reaction was evaporated to dryness under reduced pressure
  4. customby partitioning between dichloromethane and saturated aqueous sodium bicarbonate
  5. dry with materialThe organic was dried with magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe crude was purified

Sources & evidence

ORD record
ord-6c16fcb018064eb1aa669be1fa2bc002
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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