Ammonia → HCID 70921717, compound

HRID 2069128Notes

Reaction equation

HRID 2069128 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=1.CCN(C(C)C)C(C)C.[CH3:28][O:29][CH2:30][C:31](Cl)=[O:32].N>C1COCC1.CO>[CH3:28][O:29][CH2:30][C:31]([NH:12][C:8]1[CH:7]=[C:6]([O:5][C:4]2[CH:13]=[CH:14][C:15]([N+:16]([O-:18])=[O:17])=[C:2]([CH3:1])[CH:3]=2)[CH:11]=[CH:10][N:9]=1)=[O:32]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 23153294HCID 23153294, compound

Product 1

HCID 70921717HCID 70921717, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(3-methyl-4-nitrophenoxy)pyridin-2-amine (300 mg, 1.22 mmol) in THF (5.0 mL) and DIPEA (1.7 mL, 6.12 mmol) at 0° C. was added 2-methoxyacetyl chloride (447 μL, 4.89 mmol) in a single portion and the reaction mixture warmed to RT for 30 min. A solution of NH3 in MeOH (7M, 3.0 mL) was added and after 30 min at RT the mixture was evaporated in vacuo. The residue was partitioned between DCM (50 mL) and water (40 mL) and the organic phase was separated and dried (MgSO4) and was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 5% MeOH in DCM, isocratic elution) to afford 2-methoxy-N-(4-(3-methyl-4-nitrophenoxy)pyridin-2-yl)acetamide (210 mg, 53%) as a yellow oil; Rt 2.06 min (Method 2); m/z 318 (M+H)+ (ES+).

Workup

  1. customwas evaporated in vacuo
  2. customThe residue was partitioned between DCM (50 mL) and water (40 mL)
  3. customthe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. customwas evaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 40 g, 5% MeOH in DCM, isocratic elution)

Sources & evidence

ORD record
ord-55b1bcacfa984de6a3aa77b93342ad3c
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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