m-Chloroperbenzoic acid → HCID 131721929, compound

HRID 1870243Notes

Reaction equation

HRID 1870243 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[NH:19][C:20]([O:22][CH2:23][CH2:24][S:25][CH3:26])=[O:21])=[CH:8][CH:7]=[CH:6][N:5]2[C:27]=1[CH3:28].ClC1[CH:31]=[C:32](C=CC=1)[C:33]([O:35]O)=[O:34].[C:40](=[O:43])([OH:42])[O-:41].[Na+]>ClCCl>[C:33]([OH:35])(=[O:34])/[CH:32]=[CH:31]/[C:40]([OH:42])=[O:43].[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[NH:19][C:20]([O:22][CH2:23][CH2:24][S:25]([CH3:26])=[O:41])=[O:21])=[CH:8][CH:7]=[CH:6][N:5]2[C:27]=1[CH3:28].[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[NH:19][C:20]([O:22][CH2:23][CH2:24][S:25]([CH3:26])=[O:34])=[O:21])=[CH:8][CH:7]=[CH:6][N:5]2[C:27]=1[CH3:28]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 9806516HCID 9806516, compound

Product 1

HCID 131721929HCID 131721929, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,3-dimethyl-8-{2-[(2-methylsulfanylethoxy)carbonylamino]-6-methylbenzylamino}imidazo-[1,2-a]pyridine (1.0 g) in anhydrous dichloromethane (25 ml) is cooled to 0° C. and treated in portions with m-chloroperoxybenzoic acid (800 mg) and then stirred at 0° C. for a further 15 min. Aqueous sodium bicarbonate solution (25 ml) is then added, the mixture is stirred for a further 10 min, the organic phase is separated off and the aqueous phase is extracted with dichloromethane (3×20 ml). The combined organic phases are washed with water (50 ml), dried over magnesium sulfate and concentrated. To separate off the sulfone, the residue is chromatographed on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.1). The fractions of Rf =0.15 are collected and concentrated. The residue is taken up in a hot solution of fumaric acid (150 mg) in acetone (20 ml) and then cooled to 4° C. After filtration and drying in a high vacuum, 0.54 g (46%) of the title compound is isolated as a pale beige crystallizate. M.p. 137-138° C.

Workup

  1. stirringthe mixture is stirred for a further 10 min
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted with dichloromethane (3×20 ml)
  4. washThe combined organic phases are washed with water (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customTo separate off the sulfone
  8. customthe residue is chromatographed on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.1)
  9. customThe fractions of Rf =0.15 are collected
  10. concentrationconcentrated
  11. temperaturecooled to 4° C
  12. filtrationAfter filtration
  13. customdrying in a high vacuum

Sources & evidence

ORD record
ord-1e38691f900d450aab8b52dc01a2fadb
Source dataset
uspto-grants-2000_08
Patent number
US06096758

Reaction notes

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