Dimethylamine → HCID 86613792, compound

HRID 2378111Notes

Reaction equation

HRID 2378111 reaction equation
[CH3:1][NH:2][CH3:3].[CH:4]([O:7][C:8]([N:10]1[C:19]2[C:14](=[N:15][C:16](Br)=[CH:17][CH:18]=2)[C@H:13]([N:21]([C:37](=[O:39])[CH3:38])[CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[CH2:12][C@@H:11]1[CH2:40][CH3:41])=[O:9])([CH3:6])[CH3:5]>O.CS(C)=O>[CH:4]([O:7][C:8]([N:10]1[C:19]2[C:14](=[N:15][C:16]([N:2]([CH3:3])[CH3:1])=[CH:17][CH:18]=2)[C@H:13]([N:21]([C:37](=[O:39])[CH3:38])[CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[CH2:12][C@@H:11]1[CH2:40][CH3:41])=[O:9])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 86613793HCID 86613793, compound

Product 1

HCID 86613792HCID 86613792, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Add N,N-dimethylamine 40% in water (0.5 mL) to a solution of (+/-)-cis-4-[acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-2-ethyl-6-bromo-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (60 mg, 0.098 mmol) in dimethylsulfoxide (0.2 mL) and heat the mixture at 100° C. in a sealed tube for 15 h. Cool the reaction mixture to room temperature, add water and extract with ethyl acetate. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Chromatograph the residue overa silica gel cartridge, eluting with hexanes/ethyl acetate to provide the title compound (32 mg, 57%). MS (ES+): 575 (M+H).

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. extractionextract with ethyl acetate
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure
  6. washChromatograph the residue overa silica gel cartridge, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7e54c1c1683142918d2debb7804f8871
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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