Water → HCID 69002618, compound

HRID 30809Notes

Reaction equation

HRID 30809 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([NH:17][CH3:18])[C:14]([N+:19]([O-:21])=[O:20])=[CH:13][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=1.C(N(C(C)C)CC)(C)C.[C:31](Cl)(=[O:33])[CH3:32].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:16]=[C:15]([NH:17][CH3:18])[C:14]([N+:19]([O-:21])=[O:20])=[CH:13][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:31](=[O:33])[CH3:32])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 690081804-(2-Methoxy-4-(methylamino)-5-nitrophenoxy)pyridin-2-amine

Product 1

HCID 69002618HCID 69002618, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 4-(2-methoxy-4-(methylamino)-5-nitrophenoxy)-pyridin-2-amine (1 eq) and diisopropylethylamine (4 eq) in methylene chloride was brought to 0° C. Acetyl chloride (1.1 eq) was added dropwise and mixture stirred for 5 minutes. Reaction brought to room temperature and water added. Organic layer washed with brine, dried over sodium sulfate and concentrated to yield N-(4-(2-methoxy-4-(methylamino)-5-nitrophenoxy)pyridin-2-yl)acetamide. HPLC=3.21 min; MS: MH+=333.

Workup

  1. customwas brought to 0° C
  2. customReaction
  3. custombrought to room temperature
  4. washOrganic layer washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8adcb777f22a4460a4df131b3371405f
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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