Diisopropylethylamine → HCID 86762130, compound

HRID 2043462Notes

Reaction equation

HRID 2043462 reaction equation
Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:22][C@H:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH3:21])[N:11]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Product 1

HCID 86762130HCID 86762130, compoundYield 37.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5.0 g of methyl 2,6-dichloronicotinate was dissolved in ml of dimethylformamide, and 4.39 g of (S)-(−)-1-(4-fluorophenyl)ethylamine, 6.27 g of diisopropylethylamine and 150 mg of 4-dimethylaminopyridine were added thereto, and the mixture was stirred at 60° C. for 24 hours. The reaction solution was cooled, and then diluted with ethyl acetate, and washed in turn with water and brine, and the organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 2.83 g of the objective compound as white powder.

Workup

  1. additionwere added
  2. temperatureThe reaction solution was cooled
  3. washwashed in turn with water and brine
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-02c21fa0a45b451ca0380f6e0336dcdf
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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