Pyridine → HCID 25174163, compound

HRID 1966516Notes

Reaction equation

HRID 1966516 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[C:12]2[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].N1C=CC=C[CH:34]=1>>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[CH2:19][NH:18][C:12]1[C:11]2[C:16](=[C:7]([O:6][CH2:5][CH2:4][NH:3][S:29]([CH2:28][CH3:34])(=[O:31])=[O:30])[CH:8]=[CH:9][CH:10]=2)[N:15]=[C:14]([CH3:17])[CH:13]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 25217580HCID 25217580, compound

Product 1

HCID 25174163HCID 25174163, compound

Procedure

[8-(2-Aminoethoxy)-2-methylquinolin-4-yl]-(3,4-dichlorobenzyl)-amine dihydrochloride (example 20, 60 mg, 0.160 mmole) and methanesulfonyl chloride (33.8 mg, 0.30 mmole) were dissolved in pyridine and stirred at RT for 12 hrs. The content of the flask was concentrated, mixed with 1N NaOH and extracted with dichloromethane. The organic layer was washed with water and saturated NaCl solution and concentrated. The residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:methanol 95:5. After precipitation in ethyl acetate a white solid was obtained (12 mg, 17%).

Workup

  1. concentrationThe content of the flask was concentrated
  2. additionmixed with 1N NaOH
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water and saturated NaCl solution
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified
  8. washeluting with dichloromethane:methanol 95:5
  9. customAfter precipitation in ethyl acetate a white solid
  10. customwas obtained (12 mg, 17%)

Sources & evidence

ORD record
ord-11d5fb921f254fea85088b038a379c58
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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