Methanesulfonyl chloride → HCID 18923667, compound

HRID 1899991Notes

Reaction equation

HRID 1899991 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-551287cd2bb04b8d8b7718dcef59ca83
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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