Diethyl Ether → HCID 19955604, compound

HRID 1779443Notes

Reaction equation

HRID 1779443 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:10]([C:12]1[N:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[C:37](=[O:42])[C:38](=[O:41])[C:39]=3[OH:40])=[CH:26][CH:25]=2)[C:15]2=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]2[N:13]=1)[CH3:11].[I-].[K+].C(OCC)C>CN(C)C(=O)C>[C:1]([O:7][CH2:8][O:42][C:37]1[C:38](=[O:41])[C:39](=[O:40])[C:36]=1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:22]2[C:15]3=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]3[N:13]=[C:12]2[CH2:10][CH3:11])=[CH:25][CH:26]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 87885Chloromethyl pivalate2×HCID 9910945HCID 9910945, compound

Product 1

HCID 19955604HCID 19955604, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Chloromethyl pivalate (3.22 g) was added, dropwise, at ambient temperature, to a stirring suspension of 3-[4'-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyrid-3-ylmethyl)biphenyl -2-yl]-4-hydroxycyclobut-3-ene-1,2-dione (4.21 g; preparable as in Example 4) in dry N,N-dimethylacetamide (40 ml). Potassium iodide (2.5 g) was added to the resulting mixture and stirring was continued am ambient temperature for 2 days. More chloromethyl pivalate (3.7 g) was added and stirring was continued for an additional 2 days. The mixture obtained was poured into diethyl ether (500 ml) to give a gum which was separated and then dissolved in a mixture of acetone (100 ml) and ethyl acetate (300 ml). The resulting solution was washed with saturated aqueous sodium bicarbonate solution (2×400 ml) then water (2×400 ml) and dried over magnesium sulphate. The solvents were evaporated under reduced pressure and the residue obtained was purified by flash chromatography on silica gel (eluting with ethyl acetate) to give 2-[4'-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyrid-3-ylmethyl)biphenyl-2-yl]-3,4-dioxocyclobut-1-en-1-yloxymethyl pivalate, an active compound of the present invention, as a fellow foam (0.54 g) which melted slowly at 60°-80° C.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 2 days
  3. customThe mixture obtained
  4. customto give a gum which
  5. customwas separated
  6. dissolutiondissolved in a mixture of acetone (100 ml) and ethyl acetate (300 ml)
  7. washThe resulting solution was washed with saturated aqueous sodium bicarbonate solution (2×400 ml)
  8. dry with materialwater (2×400 ml) and dried over magnesium sulphate
  9. customThe solvents were evaporated under reduced pressure
  10. customthe residue obtained
  11. customwas purified by flash chromatography on silica gel (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-baa78232fb4648cdaffdaf32ac144c3e
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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