Pyridine → HCID 68776069, compound

HRID 408663Notes

Reaction equation

HRID 408663 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:23])[CH:8]=2)[N:3]=1.[C:24]1([S:30]([Cl:33])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>ClCCl.[OH-].[Na+]>[ClH:33].[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:23][S:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:32])=[O:31])[CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 68725336HCID 68725336, compound

Product 1

HCID 68776069HCID 68776069, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Methyl-6-amino-4-(3-phenylpyrrolidin-1-yl)quinoline (0.07 g; see Example 45 below), benzenesulfonyl chloride (0.041 g) and pyridine (0.04 g) was stirred in dichloromethane (4 mL). The reaction mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated to give a brown oil. The residue was purified by chromatography on silica, eluting with a mixture of dichloromethane, and methanol. The desired fractions were concentrated, hydrochloric acid was added, and the sample evaporated to dryness. Trituration from ether gave the title compound as a white solid (0.035 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a mixture of dichloromethane, and methanol
  9. concentrationThe desired fractions were concentrated
  10. additionhydrochloric acid was added
  11. customthe sample evaporated to dryness

Sources & evidence

ORD record
ord-feec5c8535964069aff91b6e4ff72ba3
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

Loading…