Methyl iodide → 3-[Methyl(methylsulfonyl)amino]-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamide

HRID 655913Notes

Reaction equation

HRID 655913 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]([NH:18][C@H:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:20][CH3:21])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:4])=[O:3].[C:34]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[CH3:34][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[C:7]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]([NH:18][C@H:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][CH3:21])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 23649245Pavinetant

Product 1

HCID 161268943-[Methyl(methylsulfonyl)amino]-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamideYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[(methylsulfonyl)amino]-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamide (1) (459 mg, 1.0 mmol) in 5 ml DMF was added Cs2CO3 (325.8 mg, 1.0 mmol) and CH3I (62.3 μL, 1.0 mmol). The reaction mixture was stirred at RT under N2 for 2 h. All solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and then concentrated in vacuo. The residue was purified by recrystallization from ether/CH2Cl2 to give the title compound (210 mg, 44.4%) as a solid. 1H NMR (300 MHz, CDCl3) δ 0.94 (t, 3H), 1.97 (m, 2H), 2.71 (s, 3H), 3.43 (s, 3H), 5.10 (q, 1H), 5.14 (b, 1H), 7.32 (d, 2H), 7.34 (d, 2H), 7.39 (m, 1H), 7.78 (m, 2H), 7.84 (m, 2H), 8.08 (m, 1H), 8.30 (m, 2H), 8.42 (m, 2H). MS APCI, m/z=474 (M+1). LCMS: 2.32 min.

Workup

  1. customAll solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by recrystallization from ether/CH2Cl2

Sources & evidence

ORD record
ord-81f2de68485d451f9c3922659b9451c0
Source dataset
uspto-grants-2011_12
Patent number
US08071621B2

Reaction notes

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