2-Chloro-N,N-dimethylethylamine → HCID 69441013, compound

HRID 1948262Notes

Reaction equation

HRID 1948262 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:15]=3)=[CH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:32][N:33]([CH2:35][CH2:36]Cl)[CH3:34]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]3[CH:19]=[CH:18][C:17]([N:20]([CH2:36][CH2:35][N:33]([CH3:34])[CH3:32])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:16][CH:15]=3)=[CH:8]2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 86614971HCID 86614971, compound

Product 1

HCID 69441013HCID 69441013, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

According to Scheme 19 Step 4: tert-Butyl 4-(1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenylcarbamate (0.34 mmol 0.14 g) was dissolved in dry THF (4 mL) and the resulting solution was cooled at 0° C. Then, NaH (60% mineral oil; 1.02 mmol, 40.8 mg) was added, the mixture was stirred at 0° C. for 10 minutes, warmed at room temperature and stirred for 30 minutes. After, N,N-dimethylaminoethyl chloride (0.69 mmol) and KI (0.34 mmol, 57.0 mg) were added and the reaction mixture was heated at 90° C. for 16 hours. The resulting suspension was taken up in CH2Cl2, washed with water, washed with brine, filtered off and the filtrate washed with CH2Cl2. The organic solvent was separated, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge (CH2Cl2/MeOH(NH3)sat. 95/5). The product fractions were collected and the solvent was evaporated to yield tert-butyl 4-(1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenyl(2-(dimethylamino)ethyl)carbamate (87.9 mg)

Workup

  1. temperaturewarmed at room temperature
  2. stirringstirred for 30 minutes
  3. temperaturethe reaction mixture was heated at 90° C. for 16 hours
  4. washwashed with water
  5. washwashed with brine
  6. filtrationfiltered off
  7. washthe filtrate washed with CH2Cl2
  8. customThe organic solvent was separated
  9. dry with materialdried (Na2SO4)
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified in a manifold (vac.)
  12. customThe product fractions were collected
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0f09741485564b058ea332059058ce67
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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