Hydrochloric Acid → HCID 57486810, compound

HRID 577772Notes

Reaction equation

HRID 577772 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][N:7]([CH2:10][C:11]1[CH:12]=[C:13]2[C:20]([CH3:21])=[N:19][N:18]([CH3:22])[C:14]2=[N:15][C:16]=1[Cl:17])[C:8]#[N:9].[N-:32]=[N+:33]=[N-:34].[Na+].Cl.C(OCC)(=O)C>O.[Br-].[Zn+2].[Br-]>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:28])([F:27])[F:29])[CH:25]=1)[CH2:6][N:7]([CH2:10][C:11]1[CH:12]=[C:13]2[C:20]([CH3:21])=[N:19][N:18]([CH3:22])[C:14]2=[N:15][C:16]=1[Cl:17])[C:8]1[N:32]=[N:33][NH:34][N:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 57486809HCID 57486809, compound

Product 1

HCID 57486810HCID 57486810, compoundYield 164.4%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 962WaterSolvent

Procedure

A mixture of (3,5-bis-trifluoromethyl-benzyl)-(6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-ylmethyl)-cyanamide (8.5 g, 10 mmol), sodium azide (1.4 g, 20 mmol), and zinc bromide (4.1 g, 10 mmol) in water (300 mL) was refluxed for 3 h. The reaction mixture was cooled to RT, 5% hydrochloric acid (50 mL) and ethyl acetate (500 mL) were added, and the resulting mixture was stirred for 20 min, after which time the organic layer was separated. This process was repeated 3 more times with ethyl acetate (3×500 mL). The combined organic layers were dried and concentrated, and the residue was purified by column chromatography over 230-400 mesh silica gel. Elution of the column with 15% ethyl acetate in hexanes gave the pure product as a colorless solid (8.3 g), yield: 90%.

Workup

  1. temperaturewas refluxed for 3 h
  2. customafter which time the organic layer was separated
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography over 230-400 mesh silica gel
  6. washElution of the column with 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b01c2df1d6d44e618eeef124b46c9341
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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