Bicarbonate Ion → HCID 22672578, compound

HRID 1369575Notes

Reaction equation

HRID 1369575 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][C:7]([CH2:20][OH:21])=[CH:6][N:5]2[C:22]=1[CH3:23].S(Cl)([Cl:26])=O.[C:28](=O)(O)[O-]>C(Cl)Cl>[ClH:26].[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:13]([CH3:19])=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:18])=[CH:8][C:7]([CH2:20][O:21][CH3:28])=[CH:6][N:5]2[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 24386Thionyl ChlorideHCID 22672592HCID 22672592, compound

Product 1

HCID 22672578HCID 22672578, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-6-hydroxymethyl-imidazo[1,2-a]pyridine (0.08 g, 0.26 mmol) in methylene chloride (5 ml) was added thionyl chloride (0.038 ml, 0.52 mmol) and the mixture was stirred for 2 h. A saturated bicarbonate solution was added and the organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. To the residue was added methanol (5 ml) the mixture was stirred overnight. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride: methanol (100:5) as eluent. Treating the residue with HCl/diethyl ether and filtration gave 0.01 g (11%) of the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure
  4. additionTo the residue was added methanol (5 ml) the mixture
  5. stirringwas stirred overnight
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel
  8. additionTreating the residue
  9. filtrationwith HCl/diethyl ether and filtration

Sources & evidence

ORD record
ord-fb2cd1522ecd41ce85118459136f3285
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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