Water → HCID 59309891, compound

HRID 1513052Notes

Reaction equation

HRID 1513052 reaction equation
[C:1]([C:4]1[N:9]=[C:8]2[N:10]([C:14]3[CH:19]=[C:18]([O:20][CH2:21][C:22]4[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]([F:30])[C:23]=4[F:31])[C:17]([O:32][CH2:33][CH2:34][OH:35])=[CH:16][C:15]=3[Cl:36])[C:11](=[O:13])[NH:12][C:7]2=[CH:6][CH:5]=1)(O)=[O:2].B.O1CCCC1.O.[Cl-].[NH4+]>O1CCCC1>[Cl:36][C:15]1[CH:16]=[C:17]([O:32][CH2:33][CH2:34][OH:35])[C:18]([O:20][CH2:21][C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]([F:30])[C:23]=2[F:31])=[CH:19][C:14]=1[N:10]1[C:8]2=[N:9][C:4]([CH2:1][OH:2])=[CH:5][CH:6]=[C:7]2[NH:12][C:11]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuranHCID 25055471HCID 25055471, compound

Product 1

HCID 59309891HCID 59309891, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-carboxy-3-[2-chloro-5-(2,3-difluoro-6-methoxybenzyl-oxy)-4-(2-hydroxyethoxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (28 mg) in tetrahydrofuran (3 mL) was added borane-tetrahydrofuran complex (1.2 mol/L tetrahydrofuran solution, 0.21 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture were added water and a saturated aqueous ammonium chloride solution, and the resulting mixture was stirred at room temperature for 5 minutes. The mixture was extracted with ethyl acetate twice, and the extracts were dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−ethyl acetate−ethyl acetate/methanol=10/1) to give the title compound (6 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate twice
  2. dry with materialthe extracts were dried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−ethyl acetate−ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-4b9efe546e854e5888d8f9433f75a0f8
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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