2-Methoxyethylamine → HCID 67458168, compound

HRID 639647Notes

Reaction equation

HRID 639647 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[C:11]([CH:26]=[CH2:27])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][O:29][CH2:30][CH2:31][NH2:32]>>[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[C:11]([CH2:26][CH2:27][NH:32][CH2:31][CH2:30][O:29][CH3:28])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 58948137HCID 58948137, compound

Product 1

HCID 67458168HCID 67458168, compoundYield 96%

Procedure

N*2*,N*4*-Dibenzyl-3-nitro-6-vinyl-pyridine-2,4-diamine (50 mg, 0.14 mmol) was suspended in 2-methoxy-ethylamine (1 ml) and the mixture refluxed for 1 h. Excess reagents was removed in vacuo, the residue dissolved in DCM (10 ml), washed with 2×H2O, dried and concentrated. The crude material was purified by column chromatography on silica, eluting with DCM:MeOH, 92:8 to give the title compound as a yellow oil, (58 mg, 96%).

Workup

  1. temperaturethe mixture refluxed for 1 h
  2. customExcess reagents was removed in vacuo
  3. dissolutionthe residue dissolved in DCM (10 ml)
  4. washwashed with 2×H2O
  5. customdried
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography on silica
  8. washeluting with DCM

Sources & evidence

ORD record
ord-693f472f02a4460581e65862d805ff70
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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