1,2-Dichloroethane → HCID 59456957, compound

HRID 1362105Notes

Reaction equation

HRID 1362105 reaction equation
Br.[NH2:2][C:3]1[N:11]=[CH:10][C:9]([Br:12])=[CH:8][C:4]=1[C:5]([OH:7])=O.CCN(CC)CC.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38]>C(Cl)Cl>[NH2:2][C:3]1[N:11]=[CH:10][C:9]([Br:12])=[CH:8][C:4]=1[C:5]([NH:38][CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 573505542-Amino-5-bromopyridine-3-carboxylic acid--hydrogen bromide (1/1)

Product 1

HCID 59456957HCID 59456957, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-amino-5-bromo-nicotinic acid hydrobromide (4.00 g, 13.4 mmol) in CH2Cl2 (150 mL) was added Et3N (2.79 mL, 20.1 mmol), EDC (2.70 g, 14.1 mmol), and HOBt (1.91 g, 14.1 mmol) at 0° C., and the mixture was stirred for 10 min. N,N-dimethylethylenediamine was then added, and the mixture was allowed to stir overnight at room temperature. The organic solution was washed with 2 N NaOH (2×20 mL), H2O (2×20 mL) and brine, dried over Na2SO4 and filtered. The solvent was concentrated to give the title compound (2.70 g, 70%) as a yellow solid: MS (ESI) m/e 287 (M+H)+.

Workup

  1. stirringto stir overnight at room temperature
  2. washThe organic solution was washed with 2 N NaOH (2×20 mL), H2O (2×20 mL) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-9205fb02785449789729b4fae9ab0f65
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…