Sodium hydride → HCID 59054343, compound

HRID 2408032Notes

Reaction equation

HRID 2408032 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[C:10]([C:13]1[CH:14]=[C:15]([CH:19]2[CH2:28][C:27]([CH3:30])([CH3:29])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:31](O)=[O:32])[CH:25]=3)[NH:20]2)[CH:16]=[CH:17][CH:18]=1)(=[O:12])[NH2:11].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[CH:1]1([S:4]([NH:7][C:31]([C:24]2[CH:25]=[C:26]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[C:10]([NH2:11])=[O:12])[CH2:28][C:27]3([CH3:30])[CH3:29])=[O:32])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70496198HCID 70496198, compound

Product 1

HCID 59054343HCID 59054343, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of cyclopropanesulfonic acid amide (200 mg, 1.65 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (66 mg, 1.65 mmol). The resulting mixture was stirred at 25° C. for 1 h to afford Solution A34. A solution of 2-(3-carbamoyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.33 mmol) and 1,1′-carbonyldiimidazole (110 mg, 0.66 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B34. Solution B34 was added to Solution A34 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 3-(6-cyclopropanesulfonylaminocarbonyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-benzamide (10 mg, 24%) as a white solid: MS (ESI) M+1=428.3.

Workup

  1. customto afford Solution A34
  2. temperaturecooled to room temperature
  3. customto afford Solution B34
  4. additionSolution B34 was added to Solution A34
  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-e127c2666d3a43ceaca17325c1d09824
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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