Sodium hydride → HCID 59054202, compound

HRID 2408019Notes

Reaction equation

HRID 2408019 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])=[CH:11][C:10]=1[CH:21]1[CH2:30][C:29]([CH3:32])([CH3:31])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:33](O)=[O:34])[CH:27]=2)[NH:22]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])=[CH:11][C:10]=1[CH:21]1[CH2:30][C:29]([CH3:31])([CH3:32])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:33]([NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[O:34])[CH:27]=2)[NH:22]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 70496784HCID 70496784, compound

Product 1

HCID 59054202HCID 59054202, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (70 mg, 1.75 mmol) in N,N-dimethylformamide (3 mL) was added methanesulfonamide (166 mg, 1.75 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A26. A solution of 2-[2-chloro-5-(2-oxo-oxazolidin-3-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.25 mmol) and 1,1′-carbonyldiimidazole (81 mg, 0.5 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B26. Solution B26 was added to Solution A26 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-{2-[2-chloro-5-(2-oxo-oxazolidin-3-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-methanesulfonamide (13 mg, 11%) as a white solid: MS (ESI) M+1=478.0.

Workup

  1. customto afford Solution A26
  2. temperaturecooled to room temperature
  3. customto afford Solution B26
  4. additionSolution B26 was added to Solution A26
  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-0ce5b942c7d34c1ba2fe70a1b3ee59d7
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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