Dibenzylamine → 4-Amino-6-bis(phenylmethyl)amino-5-nitro-pyridine-3-carboxylic acid ethyl ester

HRID 1868285Notes

Reaction equation

HRID 1868285 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:23]([O:25][C:26]([C:28]1[CH:29]=[N:30][C:31](Cl)=[C:32]([N+:35]([O-:37])=[O:36])[C:33]=1[NH2:34])=[O:27])[CH3:24]>C1(C)C=CC=CC=1>[CH2:23]([O:25][C:26]([C:28]1[CH:29]=[N:30][C:31]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:32]([N+:35]([O-:37])=[O:36])[C:33]=1[NH2:34])=[O:27])[CH3:24]

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 45588416Ethyl 4-amino-6-chloro-5-nitronicotinate

Product 1

HCID 690647034-Amino-6-bis(phenylmethyl)amino-5-nitro-pyridine-3-carboxylic acid ethyl esterYield 103.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dibenzylamine (1.95 mL, 10 mmol), triethylamine (1.37 mL, 10 mmol), 4-amino-6-chloro-5-nitro-pyridine-3-carboxylic acid ethyl ester (2.45 g, 10 mmol) and toluene (73 mL) were combined and heated at reflux over night. The reaction mixture was cooled to room temperature and filtered through a short column of silica gel (eluting first with dichloromethane then ethyl acetate). The organics were concentrated to provide 10 as a yellow oil (4.2 g). 1H NMR (400 MHz, d6-DMSO) δ: 1.28 (t, J=7.1 Hz, 3H), 4.25 (q, J=7.1 Hz, 2H), 4.60 (s, 4H), 7.14-7.31 (m, 10H), 8.35 (s, br, 2H), 8.54 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux over night
  3. filtrationfiltered through a short column of silica gel (
  4. washeluting first with dichloromethane
  5. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-bf7190ea10cb463996d1c9d6fa68aad1
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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