Bromoacetyl chloride → HCID 22254164, compound

HRID 1611711Notes

Reaction equation

HRID 1611711 reaction equation
C([O-])(O)=O.[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([NH2:26])[N:18]=2)=[CH:9][C:8]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34].[Br:35][CH2:36][C:37](Cl)=[O:38]>CCOC(C)=O>[NH2:26][C:19]1[N:18]=[C:17]([NH:16][CH2:15][CH2:14][NH:13][C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:37](=[O:38])[CH2:36][Br:35])=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[CH:9]=2)[CH:22]=[CH:21][C:20]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 22254159HCID 22254159, compound

Product 1

HCID 22254164HCID 22254164, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Aqueous NaHCO3 (8 eq) was added to the stirred solution of [4-amino-3-(2,4-dichlorophenyl)phenyl]{2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amine (1 eq) in EtOAc at room temperature. 2-bromoacetyl chloride (1.5 eq) in minimal EtOAc was added slowly to the vigorously stirred reaction solution. The reaction was monitored by LC/MS and determined to be complete within 30 min. The organic layer was separated and washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness to give the crude N-[4-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-2-(2,4-dichlorophenyl)phenyl]-2-bromoacetamide as a dark yellow glass in 76% yield (˜90% pure, LC/MS m/z 555.2 MH+). The product was stored at −4° C. to avoid decomposition.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fce090f4eefb47e1917bbe52840e5469
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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