Nicotinic Acid → Methyl-phenyl-carbamic Acid 4-{2-[(pyridine-3-carbonyl)-amino]-ethyl}-phenyl Ester

HRID 1180038

Reaction equation

HRID 1180038 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=O)[CH:2]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38](=[O:47])[N:39]([CH3:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:33][CH:32]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:28][CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][C:38](=[O:47])[N:39]([CH3:46])[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:35][CH:36]=2)=[O:9])[CH:2]=1

Participants

7

Reactant 5

HCID 938Nicotinic AcidHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 1

HCID 69517683Methyl-phenyl-carbamic Acid 4-{2-[(pyridine-3-carbonyl)-amino]-ethyl}-phenyl EsterYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-pyridinecarboxylic acid (0.3 mmol), EDAC (0.36 mmol) and triethylamine (0.36 mmol) in CH2Cl2 (10 mL) was added N-hydroxybenzoetriazole and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol). The mixture was stir-stirred 16 h at rt and purified by preparative HPLC (Gilson) to give the title compound in 15% yield as an oil.

Workup

  1. custompurified by preparative HPLC (Gilson)

Sources & evidence

ORD record
ord-dfcf06294c9041219636b8986f5ec125
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Linked notes

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