1,2-Dichloroethane → HCID 66895503, compound

HRID 1257541Notes

Reaction equation

HRID 1257541 reaction equation
[Cl-].[Na+].[Na+].[Na+].[Cl-].[Cl-].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[C:16]([CH:20]=[C:21]([CH:23]=[CH2:24])[CH:22]=2)[C:17]([OH:19])=O)=[N:12][CH:13]=1.Cl.[F:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]([NH2:35])[CH3:34])=[N:31][CH:32]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]([NH:35][C:17](=[O:19])[C:16]2[CH:20]=[C:21]([CH:23]=[CH2:24])[CH:22]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][N:12]=3)[CH:15]=2)[CH3:34])=[N:31][CH:32]=1

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 23615961Tri-sodium chlorideHCID 66690953(R)-1-(5-Fluoropyridin-2-yl)ethanamine hydrochlorideHCID 668957363-(5-Methyl-2-pyridinyl)-5-vinylbenzoic acid

Product 1

HCID 66895503HCID 66895503, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tri-sodium chloride adduct of 3-(5-methyl-2-pyridinyl)-5-vinylbenzoic acid (2.5 g, 6.0 mmol) in N,N-dimethylformamide (20 mL) were added (1R)-1-(5-Fluoropyridin-2-yl)ethanamine hydrochloride (1.60 g, 7.5 mmol), EDC (2.02 g, 10.5 mmol), HOAT (0.25 g, 1.8 mmol) and triethylamine (3.36 mL, 24 mmol). The reaction mixture was stirred at ambient temperature for 18 h. Saturated aqueous sodium bicarbonate was added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→100% ethyl acetate) gave the title compound (1.14 g). MS 362.1 (M+1).

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→100% ethyl acetate)

Sources & evidence

ORD record
ord-d514aa66fb404d55a055e81d3ee2edb5
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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