2-Bromoacetamide → HCID 21893366, compound

HRID 720459Notes

Reaction equation

HRID 720459 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-2fdec55975fa477abae5b41bf4f83277
Source dataset
uspto-grants-2006_11
Patent number
US07135486B1

Reaction notes

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