Sodium hydride → HCID 59054408, compound

HRID 2408047Notes

Reaction equation

HRID 2408047 reaction equation
[H-].[Na+].[CH:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[CH:10]1([N:13]2[C:17]([C:18]3[CH:19]=[C:20]([CH:24]4[CH2:33][C:32]([CH3:35])([CH3:34])[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([C:36](O)=[O:37])[CH:30]=5)[NH:25]4)[CH:21]=[CH:22][CH:23]=3)=[N:16][N:15]=[N:14]2)[CH2:12][CH2:11]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[CH:10]1([N:13]2[C:17]([C:18]3[CH:19]=[C:20]([CH:24]4[CH2:33][C:32]([CH3:34])([CH3:35])[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([C:36]([NH:9][S:6]([CH:3]6[CH2:5][CH2:4]6)(=[O:8])=[O:7])=[O:37])[CH:30]=5)[NH:25]4)[CH:21]=[CH:22][CH:23]=3)=[N:16][N:15]=[N:14]2)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70497734HCID 70497734, compound

Product 1

HCID 59054408HCID 59054408, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (535 mg, 13.7 mmol) in N,N-dimethylformamide (2.5 mL) was added cyclopropanesulfonamide (1.65 g, 13.8 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A41. A solution of 2-[3-(1-cyclopropyl-1H-tetrazol-5-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (544.6 mg, 1.4 mmol) and 1,1′-carbonyldiimidazole (442 mg, 2.76 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B41. Solution B41 was added to Solution A41 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-[3-(1-cyclopropyl-1H-tetrazol-5-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-amide (206.6 mg, 30%) as a white solid: MS (ESI) M+1=493.2.

Workup

  1. customto afford Solution A41
  2. temperaturecooled to room temperature
  3. customto afford Solution B41
  4. additionSolution B41 was added to Solution A41
  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-f1bae95af0fc439fa6fbb9c1ac1601f5
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

Loading…