Phenethylamine → HCID 59553897, compound

HRID 1170918Notes

Reaction equation

HRID 1170918 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([Cl:11])[N:5]=[CH:4][CH:3]=1.[CH2:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.ClCCl>[NH2:1][C:2]1[C:7]([C:8]([NH:20][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])=[C:6]([Cl:11])[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595538804-Amino-2-chloro-3-pyridinecarboxylic acid

Product 1

HCID 59553897HCID 59553897, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

4-Amino-2-chloro-nicotinic acid (1 g, 5.795 mmol) was dissolved in DMF (30 mL) and dichloromethane (50 mL). Phenethylamine (0.87 mL, 6.954 mmol, 1.2 equiv.) was added followed by TEA (1.21 mL, 8.693 mmol, 1.5 equiv.) and HBTU (2.64 g, 6.954 mmol, 1.2 equiv.) and the reaction stirred at 20° C. for 12 hours. The reaction mixture was then diluted with dichloromethane and the aqueous layer was extracted with 20% isopropyl alcohol/dichloromethane. The combined organic portions were washed with 0.5N NaOH solution, NH4Cl solution, water, brine, dried over anhydrous MgSO4, filtered and concentrated. The crude material was purified by column chromatography using 2:1 ethyl acetate:hexane to provide 1.23 g (77%) of product.

Workup

  1. extractionthe aqueous layer was extracted with 20% isopropyl alcohol/dichloromethane
  2. washThe combined organic portions were washed with 0.5N NaOH solution, NH4Cl solution, water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-e060fce251b547c4a3bad6b2f64f1d25
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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