Hydrochloric Acid → HCID 86724182, compound

HRID 873115Notes

Reaction equation

HRID 873115 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([OH:7])=O.[N:13]1([C:18]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[O:19])[CH:17]=[CH:16]N=C1.[BH4-].[Na+].Cl.O1CCC[CH2:29]1>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[CH2:5][O:7][C:17]1[CH:16]=[C:21]2[N:22]([CH3:29])[CH2:23][CH2:24][N:20]2[C:18](=[O:19])[N:13]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 149493633-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 86724182HCID 86724182, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-4,5-difluorobenzoic acid (0.75 g, 3.9 mmol) and di(1H-imidazol-1-yl)methanone (CDI) (0.695 g, 4.28 mmol) in tetrahydrofuran (THF) (10 mL) was stirred under nitrogen at room temperature for 1 h, and then a solution of NaBH4 (0.221 g, 5.84 mmol) in water (2.0 mL) was added dropwise. The reaction mixture was stirred at 10° C. for 16 h, and adjusted to pH=1 with 1 N HCl solution, concentrated to remove solvent and extracted with ethyl acetate. Separated organic part was washed with a solution of NaHCO3 and concentrated. Purification via preparative TLC afforded the title product (0.41 g).

Workup

  1. stirringThe reaction mixture was stirred at 10° C. for 16 h
  2. concentrationconcentrated
  3. customto remove solvent
  4. extractionextracted with ethyl acetate
  5. washSeparated organic part was washed with a solution of NaHCO3
  6. concentrationconcentrated
  7. customPurification via preparative TLC

Sources & evidence

ORD record
ord-dc295ae8fcfb4ed9814b42a9e4e0f634
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

Loading…