Water → HCID 68999122, compound

HRID 1821363Notes

Reaction equation

HRID 1821363 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19]2)=[N:2]1.[BH4-].[Na+].O>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19]2)=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86628206HCID 86628206, compound

Product 1

HCID 68999122HCID 68999122, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 167 (38 mg, 0.16 mmol) was dissolved in methanol (2.0 mL) and added with sodium borohydride (12 mg, 0.32 mmol) followed by stirring at room temperature for 4 hours. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated. Then, the residue was triturated in ethyl acetate to obtain Compound 168 (23 mg, 45%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. customThen, the residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-f8c95caec66d46b0ab80b89870a00ee5
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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