Sodium hydride → HCID 68172328, compound

HRID 2408070Notes

Reaction equation

HRID 2408070 reaction equation
[H-].[Na+].[CH:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[CH3:10][C:11]1([CH3:37])[C:20]2[C:15](=[C:16](C(O)=O)[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]([CH3:36])[CH2:32][CH2:31]3)[CH:25]=2)[CH2:12]1.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39]>CN(C)C=O.O>[CH3:37][C:11]1([CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:38]([NH:9][S:6]([CH:3]3[CH2:5][CH2:4]3)(=[O:8])=[O:7])=[O:39])[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]([CH3:36])[CH2:34][CH2:35]3)[CH:25]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70497760HCID 70497760, compound

Product 1

HCID 68172328HCID 68172328, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (448 mg, 11.2 mmol) in N,N-dimethylformamide (3 mL) was added cyclopropanesulfonic acid amide (1.35 g, 11.2 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A51. A solution of 4,4-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (564 mg, 1.5 mmol) and 1,1′-carbonyldiimidazole (519 mg, 3.2 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B51. Solution B51 was added to Solution A51 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-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-amide (140 mg, 10%) as a white solid: MS (ESI) M+1=483.3.

Workup

  1. customto afford Solution A51
  2. temperaturecooled to room temperature
  3. customto afford Solution B51
  4. additionSolution B51 was added to Solution A51
  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-01d7feaf821d4b0c86ade17d5f86b271
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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