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Hydrochloric Acid → N-[6-(4-amino-3-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095767
Notes
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Reaction equation

HRID 2095767 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:21]=[CH:20][C:19]([NH:22]C(=O)OCC5C=CC=CC=5)=[C:18]([F:33])[CH:17]=4)=[CH:11][N:10]3[CH:34]=2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Ba+2].[OH-].Cl>COCCOC>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:12]2[CH:13]=[CH:14][C:9]3[N:10]([CH:34]=[C:7]([NH:6][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])[N:8]=3)[CH:11]=2)=[CH:17][C:18]=1[F:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6093286Barium hydroxideHCID 58158453Benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]carbamate

Product 1

HCID 58158468N-[6-(4-amino-3-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 63%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent

Conditions

Temperature
90 °C

Procedure

To a suspension of benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]carbamate (9.7 g, 21.1 mmol) in 1,2-dimethoxyethane (291 mL) was added 0.15 mol/L aqueous barium hydroxide solution (194 mL), and the mixture was stirred at 90° C. for 16 hr. After cooling to room temperature, the reaction mixture was adjusted to about pH 8 with 2N hydrochloric acid, and extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate and collected by filtration to give the title compound (4.3 g, 63%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate/tetrahydrofuran
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residue was washed with ethyl acetate
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5c5cea062a504183a2ddbd12b7b7996f
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08445509B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes