Sodium hydride → HCID 23557335, compound

HRID 1694847Notes

Reaction equation

HRID 1694847 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12](=[O:27])[CH2:13][C:14]([NH:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)=[O:15])[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH:31]([CH2:37][CH2:38][CH2:39][CH3:40])[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C.C1COCC1>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][CH2:37][CH2:38][CH2:39][CH2:40][CH:13]([C:14](=[O:15])[NH:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][CH:23]=[CH:22]2)[C:12](=[O:27])[NH:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2)[CH3:36]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79072Ethyl 2-bromohexanoateHCID 12107974HCID 12107974, compound

Product 1

HCID 23557335HCID 23557335, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,N′-di-quinolin-8-yl-malonamide (10.3 g, 28.8 mmol) in dry DMF (200 mL) and dry THF (85 mL) at 0° C. was added NaH (60% disp./1.27 g, 31.7 mmol) portion-wise. The resultant solution was allowed to warm to RT for 10 min. The solution was cooled to 0° C. and ethyl bromohexanoate (5.6 mL, 31.7 mmol) was added dropwise. The mixture was stirred overnight. The solvent was removed, and the residue was diluted with EtOAc (250 mL), and washed with H2O (100 mL). The organic fraction was dried, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to yield the desired material (10 g, 69.6%). ESIMS calcd 499 (M++H), found 499 (M++H).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe solvent was removed
  3. additionthe residue was diluted with EtOAc (250 mL)
  4. washwashed with H2O (100 mL)
  5. customThe organic fraction was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-106981c0e3bd46e197babcd59da7b39f
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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