Methylamine → (2-Amino-6-methylamino-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

HRID 639668Notes

Reaction equation

HRID 639668 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:5][C:6](=[O:26])[N:7]([C:15]1[CH:20]=[C:19](Br)[N:18]=[C:17]([NH2:22])[C:16]=1[N+:23]([O-:25])=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4]>C1COCC1>[CH2:3]([O:5][C:6](=[O:26])[N:7]([C:15]1[CH:20]=[C:19]([NH:2][CH3:1])[N:18]=[C:17]([NH2:22])[C:16]=1[N+:23]([O-:25])=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86614485(2-Amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

Product 1

HCID 67455106(2-Amino-6-methylamino-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (40% solution in water) (0.055 ml) was added to a solution of (2-amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester (50 mg) in THF (0.5 ml) at room temperature. The reaction was stirred under nitrogen for 16 hours then the solution pre-absorbed directly onto silica gel. The mixture was purified by chromatography on an Isco Companion, eluting with ethyl acetate:heptane, increasing the gradient linearly from 20:80 to 60:40 over several column volumes. The desired fractions were combined and evaporated to provide the title compound (30 mg) as a yellow gum.

Workup

  1. customthe solution pre-absorbed directly onto silica gel
  2. customThe mixture was purified by chromatography on an Isco Companion
  3. washeluting with ethyl acetate
  4. temperatureheptane, increasing the gradient linearly from 20:80 to 60:40 over several column volumes
  5. customevaporated

Sources & evidence

ORD record
ord-d0f236409b9c435791ac9552621f28ee
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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