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

HRID 1920984Notes

Reaction equation

HRID 1920984 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-802bfa132aae445485b5e1dc945bfa06
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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