Sodium hydride → HCID 59053439, compound

HRID 2408060Notes

Reaction equation

HRID 2408060 reaction equation
[H-].[Na+].[CH:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[CH2:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:14][C:13]=1[CH:24]1[CH2:33][C:32]([CH3:35])([CH3:34])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:36](O)=[O:37])[CH:30]=2)[NH:25]1)[CH3:11].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[CH2:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:14][C:13]=1[CH:24]1[CH2:33][C:32]([CH3:34])([CH3:35])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:36]([NH:9][S:6]([CH:3]3[CH2:5][CH2:4]3)(=[O:8])=[O:7])=[O:37])[CH:30]=2)[NH:25]1)[CH3:11]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70496022HCID 70496022, compound

Product 1

HCID 59053439HCID 59053439, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (356 mg, 8.9 mmol) in N,N-dimethylformamide (4 mL) was added cyclopropanesulfonic acid amide (1 g, 8.9 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A47. A solution of 2-(2-ethyl-5-morpholin-4-yl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (500 mg, 1.27 mmol) and 1,1′-carbonyldiimidazole (412 mg, 2.54 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B47. Solution B47 was added to Solution A47 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-ethyl-5-morpholin-4-yl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (100 mg, 15%) as a white solid: MS (ESI) M+1=498.1.

Workup

  1. customto afford Solution A47
  2. temperaturecooled to room temperature
  3. customto afford Solution B47
  4. additionSolution B47 was added to Solution A47
  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-bb8eecd0d0324c9db0c140730149c889
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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