Sodium hydride → HCID 59054269, compound

HRID 2408022Notes

Reaction equation

HRID 2408022 reaction equation
[H-].[Na+].[CH:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][CH2:20][O:19][C:18]2=[O:22])=[CH:13][C:12]=1[CH:23]1[CH2:32][C:31]([CH3:34])([CH3:33])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:35](O)=[O:36])[CH:29]=2)[NH:24]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][CH2:20][O:19][C:18]2=[O:22])=[CH:13][C:12]=1[CH:23]1[CH2:32][C:31]([CH3:33])([CH3:34])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:35]([NH:9][S:6]([CH:3]3[CH2:5][CH2:4]3)(=[O:8])=[O:7])=[O:36])[CH:29]=2)[NH:24]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70496784HCID 70496784, compound

Product 1

HCID 59054269HCID 59054269, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (176 mg, 4.4 mmol) in N,N-dimethylformamide (3 mL) was added cyclopropanesulfonic acid amide (530 mg, 4.4 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A29. 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 (250 mg, 0.62 mmol) and 1,1′-carbonyldiimidazole (203 mg, 1.25 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B29. Solution B29 was added to Solution A29 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 cyclopropanesulfonic acid {2-[2-chloro-5-(2-oxo-oxazolidin-3-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-amide (85 mg, 27%) as a white solid: MS (ESI) M+1=504.0.

Workup

  1. customto afford Solution A29
  2. temperaturecooled to room temperature
  3. customto afford Solution B29
  4. additionSolution B29 was added to Solution A29
  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-0f8caa7c39534247ba7682b58df8d02b
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

Loading…