Methanesulfonyl chloride → HCID 18923667, compound

HRID 1290174Notes

Reaction equation

HRID 1290174 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:5]([Cl:24])=[C:6]([C:20]([Cl:23])=[CH:21][CH:22]=1)[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([Br:19])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1.CS(Cl)(=O)=O>N1C=CC=CC=1.C(N(CC)C=O)C>[Br:19][C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]3[C:20]([Cl:23])=[CH:21][CH:22]=[C:4]([N:3]=[CH:15][N:11]([CH2:12][CH3:13])[CH2:10][CH3:9])[C:5]=3[Cl:24])[C:10]2=[N:17][C:16]=1[CH3:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 189233178-(3-Amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride

Product 1

HCID 18923667HCID 18923667, compoundYield 127.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 12051DiethylformamideSolvent

Procedure

To a suspension of 8-(3-amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride (100 mg) in a mixture of pyridine (0.5 ml) and N,N-diethylformamide (1.5 ml) was added methanesulfonyl chloride (27 mg) in one portion. The mixture was stirred at 60°-70° C. for one and half hours, cooled, and poured into ice water. The separated oil was extracted with dichloromethane. The extract was washed with water, dried, and concentrated in vacuo to give a brown oil, which was purified by preparative thin-layer chromatography on silica gel (5% solution of methanol in dichloromethane) to give 3-bromo-8-[2,6-dichloro-3-[(N,N-diethylaminomethylene)amino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (65 mg) as crystals.

Workup

  1. temperaturecooled
  2. extractionThe separated oil was extracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil, which
  7. customwas purified by preparative thin-layer chromatography on silica gel (5% solution of methanol in dichloromethane)

Sources & evidence

ORD record
ord-8c0dd16205914d779e62c594a3cb620f
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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