Pyridine → HCID 56966356, compound

HRID 1036967Notes

Reaction equation

HRID 1036967 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][C:8]1[CH:9]=[C:10]([CH:14]2[CH2:23][C:22]([CH3:25])([CH3:24])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]#[N:27])[CH:20]=3)[NH:15]2)[CH:11]=[CH:12][CH:13]=1.N1C=CC=CC=1>ClCCl>[C:26]([C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]([C:10]1[CH:9]=[C:8]([NH:7][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:13]=[CH:12][CH:11]=1)[CH2:23][C:22]2([CH3:25])[CH3:24])#[N:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 67289758HCID 67289758, compound

Product 1

HCID 56966356HCID 56966356, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (104 mg, 0.81 mmol) was added dropwise to a mixture of 2-(3-amino-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (150 mg, 0.54 mmol) and pyridine (77 mg, 0.97 mmol) in dichloromethane (5 mL). The resultant mixture was allowed to stir overnight. The reaction mixture was washed by water, dried over magnesium sulfate. It was filtered and concentrated to provide the crude product. It was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1) to afford ethanesulfonic acid [3-(6-cyano-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide as off-white solid (120 mg, yield: 60.0%). MS (ESI+APCI) M+1=370.2.

Workup

  1. washThe reaction mixture was washed by water
  2. dry with materialdried over magnesium sulfate
  3. filtrationIt was filtered
  4. concentrationconcentrated
  5. customto provide the crude product
  6. customIt was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-afce1ad9a86c4c48be35ada486d56017
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

Loading…