Hydrochloric Acid → HCID 86591954, compound

HRID 1294072Notes

Reaction equation

HRID 1294072 reaction equation
C([NH:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[N:11]3[C:15]([CH:16]=[CH:17][CH:18]=2)=[N:14][C:13]([NH:19][C:20](=[O:23])[O:21][CH3:22])=[CH:12]3)=[CH:7][CH:6]=1)(=O)C.Cl.[NH4+].[OH-]>O>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[N:11]3[C:15]([CH:16]=[CH:17][CH:18]=2)=[N:14][C:13]([NH:19][C:20](=[O:23])[O:21][CH3:22])=[CH:12]3)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86591955HCID 86591955, compound

Product 1

HCID 86591954HCID 86591954, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-(4-acetamidophenoxy)pyridine-2-ylamine (Intermediate 9J170.2 mg, 0.7 mmol) in DMF (2 mL) was added N-(methoxycarbonyl)chloroacetoamide (159.0 mg, 1.1 mmol). The mixture was stirred at 80° C. overnight. Additional N-(methoxycarbonyl)chloroacetoamide (159.0 mg, 1.1 mmol) was added and stirred at 80° C. overnight. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with NaHCO3 (aq) and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave methyl (5-(4-acetoamidophenoxy)azaindolizine-2-yl)carbamate (51.7 mg, 22%). To a solution of methyl (5-(4-acetoamidophenoxy)azaindolizine-2-yl)carbamate (34.0 mg, 0.1 mmol) in water (2 mL) was added 2N HCl (aq) (2.0 mL) then refluxed for 1 hr and stirred at room temperature for 1 hr. The mixture was added NH4OH (aq). Formed precipitate was collected by filtration, washed with water then dried under reduced pressure to give the title compound (22.0 mg, 74%): MS m/e 299 (M+1).

Workup

  1. temperaturethen refluxed for 1 hr
  2. customFormed precipitate
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-078e33de22934c97ad9afea18fc7d5af
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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