Triethylamine → HCID 86755347, compound

HRID 1005428Notes

Reaction equation

HRID 1005428 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH2:7](N(CC)CC)C.[NH2:14][C:15]1[C:16](=[O:31])[N:17]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:18]=[CH:19][C:20]=1[CH3:21]>C(Cl)Cl.CN(C)C=O.CN(C1C=CN=CC=1)C>[C:1]([NH:14][C:15]1[C:16](=[O:31])[N:17]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:18]=[CH:19][C:20]=1[CH3:21])(=[O:5])[CH2:2][CH3:7]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21706524HCID 21706524, compound

Product 1

HCID 86755347HCID 86755347, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(R,S)-(2-naphthylacetyl)amino-3-[4'-(1"-t butoxycarbonyl-1"-methyl)ethyl]benzenepropanoic acid (0.31 g, 0.66 mmol) in methylene chloride (5 mL) at rt was added dimethylformamide (3drops) followed by oxalyl chloride (2 M in methylene chloride, 0.30 mL, 0.66 mmol). The mixture was stirred at rt for 1 hour. Triethylamine (0. 13 mL), 4-amino-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.12 g, 0.47 mmol) and DMAP (0.005 g)were added. The mixture was stirred overnight at rt, and heated at reflux for 6 hours. The solvents were evaporated, and the residue was fractionated over silica gel (ethyl acetate/hexane 1/1) to give 4-[2'-(R,S)-2""-naphthylacetyl)amino-3'-[4"-(1'"-t butoxycarbonyl-1'"-methyl)ethyl]benzene]propanoylamino-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.08 g, 0.11 mmol, 17%).

Workup

  1. stirringThe mixture was stirred overnight at rt
  2. temperatureheated
  3. temperatureat reflux for 6 hours
  4. customThe solvents were evaporated

Sources & evidence

ORD record
ord-c836d0a99e4b4b0c97f11bbe27cbb71c
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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