Sodium hydride → HCID 59053631, compound

HRID 2408101Notes

Reaction equation

HRID 2408101 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([C:19](O)=[O:20])[CH:18]=1)[NH:15][CH:14]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[CH2:32][CH2:31][O:30][C:29]3=[O:33])[CH:23]=1)[CH2:13][C:12]2([CH3:35])[CH3:34].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([C:19]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:20])[CH:18]=1)[NH:15][CH:14]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[CH2:32][CH2:31][O:30][C:29]3=[O:33])[CH:23]=1)[CH2:13][C:12]2([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 70496923HCID 70496923, compound

Product 1

HCID 59053631HCID 59053631, compoundYield 7.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of methanesulfonamide (665 mg, 7 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (280 mg, 7 mmol). The resulting mixture was stirred at 25° C. for 1 h to afford Solution A64. A solution of 6-chloro-4,4-dimethyl-2-[3-(2-oxo-oxazolidin-3-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (400 mg, 1 mmol) and 1,1′-carbonyldiimidazole (325 mg, 2 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B64. Solution B64 was added to Solution A64 and the resulting mixture was stirred at 25° C. for 1 h. To the reaction mixture was added water (0.5 mL). The mixture was filtered to remove the insoluble solid, and the filtrate was purified by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded N-{6-chloro-4,4-dimethyl-2-[3-(2-oxo-oxazolidin-3-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carbonyl}-methanesulfonamide (37 mg, 7%) as a white solid: MS (ESI) M+1=478.0.

Workup

  1. customto afford Solution A64
  2. temperaturecooled to room temperature
  3. customto afford Solution B64
  4. additionSolution B64 was added to Solution A64
  5. stirringthe resulting mixture was stirred at 25° C. for 1 h
  6. filtrationThe mixture was filtered
  7. customto remove the insoluble solid
  8. customthe filtrate was purified by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-d86e717d01474788b351937ad56f5e94
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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