Dimethylformamide → HCID 68997573, compound

HRID 1821370Notes

Reaction equation

HRID 1821370 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[C:18]2[N:22]=[C:21]([C:23](O)=[O:24])[O:20][N:19]=2)=[N:2]1.S(Cl)(Cl)=O.CN(C=O)C.[BH4-].[Na+]>C(Cl)Cl.O>[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[C:18]2[N:22]=[C:21]([CH2:23][OH:24])[O:20][N:19]=2)=[N:2]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 4311764Sodium borohydrideHCID 69003606HCID 69003606, compound

Product 1

HCID 68997573HCID 68997573, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(E)-3-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}[1,2,4]oxadiazole-5-carboxylic acid (14 mg, 0.04 mmol) obtained in Step 2 of Example 175 was dissolved in methylene chloride (1.0 mL), and thionyl chloride (5 μL, 239-0.06 mmol) and DMF (few drops) were added thereto, followed by stirring for 30 minutes. Then the mixture was concentrated and the residue was dissolved in dioxane (1.0 mL). Sodium borohydride (16 mg, 0.42 mmol) was added to the solution and the mixture was stirred at room temperature for 1 hour. Water was added to stop the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by preparative thin-layer chromatography (chloroform/acetone=4/1) to obtain Compound 179 (3.5 mg, 26%).

Workup

  1. concentrationThen the mixture was concentrated
  2. dissolutionthe residue was dissolved in dioxane (1.0 mL)
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated
  7. customthe residue was purified by preparative thin-layer chromatography (chloroform/acetone=4/1)

Sources & evidence

ORD record
ord-bda5f0e0f02448a7bd45a12e9df89700
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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