2-Bromoacetamide → HCID 21893366, compound

HRID 1784912Notes

Reaction equation

HRID 1784912 reaction equation
C[NH+]1CCOCC1.[NH2:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:12]([C:28]#[N:29])=[C:11]([SH:30])[N:10]=1.Br[CH2:32][C:33]([NH2:35])=[O:34].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:18]=[CH:19][C:20]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)[C:12]([C:28]#[N:29])=[C:11]([S:30][CH2:32][C:33]([NH2:35])=[O:34])[N:10]=1

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 516892Sodium BicarbonateHCID 178486203HCID 178486203, compound

Product 1

HCID 21893366HCID 21893366, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

135 mg (0.316 mmol) of 2-[4-(2-amino-3,5-dicyano-6-sulfanyl-4-pyridinyl)-phenoxy]acetic acid N-methylmorpholinium salt together with 103.3 mg (0.474 mmol) of bromoacetamide and 106.1 mg (1.263 mmol) of NaHCO3 are stirred in 0.5 ml of DMF overnight. After filtration, the reaction solution is prepurified by preparative HPLC. The isolated fraction is reconcentrated under reduced pressure and the residue is purified by preparative thin-layer chromatography.

Workup

  1. filtrationAfter filtration
  2. customthe residue is purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-724d98e1f7214e958705c4e6bea3c13b
Source dataset
uspto-grants-2009_03
Patent number
US07504421B2

Reaction notes

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