Sodium hydride → HCID 59053822, compound

HRID 2408124Notes

Reaction equation

HRID 2408124 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[CH3:10][C:11]1([CH3:42])[C:20]2[C:15](=[C:16]([C:21](O)=[O:22])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]3[CH2:35][CH2:34][N:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:32][CH2:31]3)[CH:25]=2)[CH2:12]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[CH3:10][C:11]1([CH3:42])[C:20]2[C:15](=[C:16]([C:21]([NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[O:22])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]3[CH2:31][CH2:32][N:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:34][CH2:35]3)[CH:25]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70496588HCID 70496588, compound

Product 1

HCID 59053822HCID 59053822, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of cyclopropanesulfonic acid amide (96 mg, 0.8 mmol) in N,N-dimethylformamide (1.5 mL) was added sodium hydride (32 mg, 0.8 mmol). The resulting mixture was stirred at 25° C. for 1 h to afford Solution A76. A solution of 4,4-dimethyl-2-[3-(4-phenyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (50 mg, 0.11 mmol) and 1,1′-carbonyldiimidazole (37 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B76. Solution B76 was added to Solution A76 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 {4,4-dimethyl-2-[3-(4-phenyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carbonyl}-amide (15 mg, 24%) as a white solid: MS (ESI) M+1=545.2.

Workup

  1. customto afford Solution A76
  2. temperaturecooled to room temperature
  3. customto afford Solution B76
  4. additionSolution B76 was added to Solution A76
  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-9f1d0473a9ca4a938516a3f3d94f93a9
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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