Sodium hydride → HCID 59053630, compound

HRID 2408099Notes

Reaction equation

HRID 2408099 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([C:21](O)=[O:22])[CH:20]=1)[NH:17][CH:16]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:25]=1)[CH2:15][C:14]2([CH3:37])[CH3:36].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O.O>[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([C:21]([NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[O:22])[CH:20]=1)[NH:17][CH:16]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:25]=1)[CH2:15][C:14]2([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 15765418CyclopropanesulfonamideHCID 70496684HCID 70496684, compound

Product 1

HCID 59053630HCID 59053630, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of cyclopropanesulfonic acid amide (1.1 g, 9.1 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (361 mg, 9 mmol). The resulting mixture was stirred at 25° C. for 1 h to afford Solution A63. A solution of 6-chloro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (520 mg, 1.3 mmol) and 1,1′-carbonyldiimidazole (422 mg, 2.6 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B63. Solution B63 was added to Solution A63 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 [6-chloro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carbonyl]-amide (25 mg, 4%) as a white solid: MS (ESI) M+1=504.2.

Workup

  1. customto afford Solution A63
  2. temperaturecooled to room temperature
  3. customto afford Solution B63
  4. additionSolution B63 was added to Solution A63
  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-64c6d2cb001e43a9863e45981512b677
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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