Hydrochloric Acid → HCID 59309931, compound

HRID 1513046Notes

Reaction equation

HRID 1513046 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([S:10]([C:13]([CH3:21])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])(=[O:12])=[O:11])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([C:32]([O:34]CC)=[O:33])=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:37].O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[C:32]([C:28]1[N:27]=[C:26]2[N:22]([C:3]3[CH:4]=[C:5]([S:10]([C:13]([CH3:14])([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH3:21])(=[O:12])=[O:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=3[Cl:1])[C:23](=[O:37])[NH:24][C:25]2=[C:30]([CH3:31])[CH:29]=1)([OH:34])=[O:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 593098103-[2-chloro-4-methoxy-5-(1-methyl-1-phenylethylsulfonyl)-phenyl]-5-ethoxycarbonyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 59309931HCID 59309931, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-[2-chloro-4-methoxy-5-(1-methyl-1-phenylethylsulfonyl)-phenyl]-5-ethoxycarbonyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (36 mg), tetrahydrofuran (2 mL), methanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (56 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was acidified by adding 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (33 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-30ce672f1605433cbd09ec7d9d1c4b62
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

Loading…