Hydrochloric Acid → HCID 68513743, compound

HRID 1513053Notes

Reaction equation

HRID 1513053 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:38])=[C:24]([N:26]3[C:30]4=[N:31][C:32]([CH2:35][OH:36])=[CH:33][CH:34]=[C:29]4[NH:28][C:27]3=[O:37])[CH:25]=2)=[C:16]([F:39])[C:15]([F:40])=[CH:14][CH:13]=1)=O)(C)(C)C.Cl>C(OCC)C>[ClH:38].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:38])=[C:24]([N:26]3[C:30]4=[N:31][C:32]([CH2:35][OH:36])=[CH:33][CH:34]=[C:29]4[NH:28][C:27]3=[O:37])[CH:25]=2)=[C:16]([F:39])[C:15]([F:40])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59309850HCID 59309850, compound

Product 1

HCID 68513743HCID 68513743, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 3-(5-{6-[2-(tert-butoxycarbonylamino)ethoxy]-2,3-difluorobenzyloxy}-2-chloro-phenyl)-5-hydroxymethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (40 mg) was added hydrochloric acid (4 mol/L ethyl acetate solution, 2 mL), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added diethyl ether, and the precipitated crystals were collected by filtration. The collected crystals were washed with diethyl ether, and dried under reduced pressure to give 3-{5-[6-(2-aminoethoxy)-2,3-difluorobenzyloxy]-2-chlorophenyl}-5-hydroxymethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one hydrochloride (12 mg). To this material were added methylene chloride (2 mL), tetrahydrofuran (1 mL), pyridine (0.1 mL) and acetic anhydride (0.003 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=10/1) to give the title compound (10 mg).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washThe collected crystals were washed with diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-823adc2b75c1413888ecca155fa37b14
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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