1,2-Dichloroethane → HCID 22593768, compound

HRID 225859

Reaction equation

HRID 225859 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 22593768HCID 22593768, compound

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 tide 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-8ed8095a5dcd4090ad564ade28f5b802
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Linked notes

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