HCID 21949856, compound → HCID 21949766, compound

HRID 2215330Notes

Reaction equation

HRID 2215330 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([CH2:16][CH3:17])[C:12]=1[O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([F:27])[CH:26]=1)[C:22]#[N:23])C1C=CC=CC=1>ClCCl.[Fe](Cl)(Cl)Cl>[CH2:16]([C:13]1[C:12]([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[C:25]([F:27])[CH:26]=2)[C:22]#[N:23])=[C:11]([CH2:10][CH2:9][OH:8])[NH:15][N:14]=1)[CH3:17]

Participants

4

Reactant 1

HCID 21949856HCID 21949856, compound

Product 1

HCID 21949766HCID 21949766, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent2×

Procedure

Iron(III)chloride (9.30 g, 57.5 mmol) was added to a solution of the pyrazole from Example 147 (2.10 g, 5.75 mmol) in dichloromethane (90 ml) under nitrogen at room temperature. After stirring for 20 minutes the mixture was diluted with dichloromethane (50 ml), washed with water (100 ml) then saturated aqueous sodium ethylenediaminetetraacetate solution (70 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 changing to 95:5, by volume) to provide the title compound (1.2 g) as a brown oil which solidified on standing.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialsaturated aqueous sodium ethylenediaminetetraacetate solution (70 ml), dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 changing to 95:5, by volume)

Sources & evidence

ORD record
ord-fc5cbb5540cd4cf0b5c2f9c55d92f098
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

Loading…