Ammonia → HCID 70921728, compound

HRID 2069136Notes

Reaction equation

HRID 2069136 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33].N>C(Cl)Cl.CO>[CH3:29][O:30][CH2:31][C:32]([NH:13][C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:16]([N+:17]([O-:19])=[O:18])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:12]=[CH:11][N:10]=1)=[O:33]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 58564784HCID 58564784, compound

Product 1

HCID 70921728HCID 70921728, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(3-methoxy-4-nitrophenoxy)pyridin-2-amine (420 mg, 1.61 mmol) in DCM (4.0 mL) containing DIPEA (562 μL, 3.22 mmol) at 0° C. was added 2-methoxyacetyl chloride (220 μL, 2.41 mmol) in a single portion. The reaction mixture was warmed to RT for 1 hr and then a solution of NH3 in MeOH (7M, 2.0 mL) was added. The resulting mixture was kept at RT for 30 min, was evaporated in vacuo and the residue was partitioned between DCM (5.0 mL) and water (5.0 mL). The organic phase was separated and evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution) to afford 2-methoxy-N-(4-(3-methoxy-4-nitrophenoxy)pyridin-2-yl)acetamide as pale yellow oil (401 mg, 75%); Rt 1.87 min (Method 2); m/z 334 (M+H)+ (ES+).

Workup

  1. customwas evaporated in vacuo
  2. customthe residue was partitioned between DCM (5.0 mL) and water (5.0 mL)
  3. customThe organic phase was separated
  4. customevaporated in vacuo
  5. customthe residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution)

Sources & evidence

ORD record
ord-4e3ece424d30415d8f87b440f7570177
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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