4-Methoxybenzylamine → HCID 89963950, compound

HRID 1749086Notes

Reaction equation

HRID 1749086 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9](Cl)[N:8]=1)[CH3:5].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>CCO>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[N:8]=1)[CH3:5]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 54223679N-(6-Chloro-3-nitro-2-pyridyl)-alanine methyl ester

Product 1

HCID 89963950HCID 89963950, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-2-(6-chloro-3-nitro-pyridin-2-ylamino)-propionic acid methyl ester (1.90 g, 7.3 mmol, 1.0 equiv) in EtOH (20 mL) was added 4-methoxy-benzylamine (1.4 mL, 11.0 mmol, 1.5 equiv) and the reaction mixture was stirred at ambient temperature for 16 h. The solvent was evaporated and the crude product was triturated with methanol to afford (S)-2-[6-(4-methoxy-benzylamino)-3-nitro-pyridin-2-ylamino]-propionic acid methyl ester (1.5 g) as a yellow solid. MS: [M+H]+=361.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was triturated with methanol

Sources & evidence

ORD record
ord-85262cbc4bcd4799a315e04697d4086f
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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