Sodium hydride → HCID 53492111, compound

HRID 1801099Notes

Reaction equation

HRID 1801099 reaction equation
[H-].[Na+].[CH2:3]([S:5]([NH2:8])(=[O:7])=[O:6])[CH3:4].[CH3:9][C:10]1([CH3:35])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20](O)=[O:21])[CH:17]=2)[NH:12][CH:11]1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:24]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[CH3:9][C:10]1([CH3:35])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]([NH:8][S:5]([CH2:3][CH3:4])(=[O:7])=[O:6])=[O:21])[CH:17]=2)[NH:12][CH:11]1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:24]=1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 73702Ethanesulfonamide2×HCID 58476241HCID 58476241, compound

Product 1

HCID 53492111HCID 53492111, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (745 mg, 18.6 mmol) in N,N-dimethylformamide (2.5 mL) was added ethanesulfonamide (2.3 g, 19 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h. A solution of 3,3-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (690 mg, 1.9 mmol) and 1,1′-carbonyldiimidazole (650 mg, 3.8 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 70° C. After stirring at 70° C. for 1 h, the above suspension of ethanesulfonamide and sodium hydride in N,N-dimethylformamide was added and the mixture was allowed to stir at 25° C. for 1 h. Purification 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 ethanesulfonic acid [3,3-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (347 mg, 40%) as a white solid: LC/MS m/e calcd for C24H31N3O4S (M+H)+: 458.61, observed: 458.0.

Workup

  1. stirringAfter stirring at 70° C. for 1 h
  2. additionwas added
  3. stirringto stir at 25° C. for 1 h
  4. customPurification 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-60120a0cffbb43aca74cebb83c98529d
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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