HCID 67431176, compound → HCID 58459169, compound

HRID 2036631Notes

Reaction equation

HRID 2036631 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[N:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[C:12]2[C:13]([N:18]=1)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:9])(C)(C)C.FC1C=C(N2C3C(=NC=CC=3)N=C2C(NC(=O)C)C)C=C(F)C=1>Cl>[F:26][C:21]1[CH:20]=[C:19]([N:11]2[C:12]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:18]=[C:10]2[CH:8]([NH2:7])[CH3:9])[CH:24]=[C:23]([F:25])[CH:22]=1

Participants

4

Reactant 2

HCID 67431176HCID 67431176, compoundHCID 67432759HCID 67432759, compound

Product 1

HCID 58459169HCID 58459169, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

A crude mixture of {{1-[1-(3,5-difluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-carbamic acid tert-butyl ester and N-{1-[1-(3,5-difluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-acetamide (300 mg) was suspended in methanolic HCl (3 mL). The reaction mixture was stirred at 70° C. for 12 h. After completion of the reaction, the solvent was removed under vacuum. The residue was suspended in water and basified using satd sodium bicarbonate solution and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 1-[1-(3,5-difluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]-ethylamine: LC-MS (ESI) m/z 275.1 [M+H]+. The crude product was used without further purification.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under vacuum
  3. extractionbasified using satd sodium bicarbonate solution and extracted with EtOAc
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b628f8fae81f4d4290e8ab7170e0d40a
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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