1,2-Dichloroethane → 2-Amino-5-bromo-N-(2-hydroxyethyl)nicotinamide

HRID 1710503Notes

Reaction equation

HRID 1710503 reaction equation
C(Cl)CCl.[NH2:5][C:6]1[N:14]=[CH:13][C:12]([Br:15])=[CH:11][C:7]=1[C:8]([OH:10])=O.[CH2:16]([CH2:18][NH2:19])[OH:17].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[NH2:5][C:6]1[N:14]=[CH:13][C:12]([Br:15])=[CH:11][C:7]=1[C:8]([NH:19][CH2:18][CH2:16][OH:17])=[O:10]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7374452-Amino-5-bromonicotinic acid

Product 1

HCID 225937682-Amino-5-bromo-N-(2-hydroxyethyl)nicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (2.91 g, 15.2 mmole) was added to a solution 2-amino-5-bromonicotinic acid (3.00 g, 13.8 mmole), ethanolamine (0.93 g, 15.2 mmole), HOBt.H2O (2.05 g, 15.2 mmole), and diisopropylethylamine (2.64 mL, 15.2 mmole) in DMF (50 mL) at RT and the reaction solution was stirred overnight. The reaction contents were poured into H2O (200 mL) and the resulting mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were washed with H2O and brine and then dried over Na2SO4. Concentration of the organic extracts afforded the title compound as a yellow solid which was used without further purification: MS (ES) m/e 261 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionthe resulting mixture was extracted with EtOAc (2×200 mL)
  3. washThe combined organic extracts were washed with H2O and brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-cf159aa952c642b1b5ac11c8d3871a10
Source dataset
uspto-grants-2010_09
Patent number
US07790716B2

Reaction notes

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