2-Bromoacetamide → HCID 21893338, compound

HRID 720458Notes

Reaction equation

HRID 720458 reaction equation
C[NH+]1CCOCC1.[NH2:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:12]([C:33]#[N:34])=[C:11]([SH:35])[N:10]=1.Br[CH2:37][C:38]([NH2:40])=[O:39].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:8][C:9]1[N:10]=[C:11]([S:35][CH2:37][C:38]([NH2:40])=[O:39])[C:12]([C:33]#[N:34])=[C:13]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 516892Sodium BicarbonateHCID 178481107HCID 178481107, compound

Product 1

HCID 21893338HCID 21893338, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

84 mg (0.163 mmol) of 2-amino-4-{4-[(4-methylpiperazino)sulfonyl]phenyl}-6-sulfanyl-3,5-pyridinedicarbonitrile N-methylmorpholinium salt together with 53.3 mg (0.244 mmol) of bromoacetamide and 54.7 mg (0.65 mmol) of NaHCO3 are stirred in 0.5 ml of DMF overnight. After filtration, the reaction solution is initially purified 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 reaction solution is initially purified by preparative HPLC
  3. customthe residue is purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-0bc141917f6e47fa99fd8858c6e22bb6
Source dataset
uspto-grants-2006_11
Patent number
US07135486B1

Reaction notes

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