1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amide

HRID 2357883Notes

Reaction equation

HRID 2357883 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[C:42]1([CH2:48][CH2:49][CH2:50][NH2:51])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl>[C:42]1([CH2:48][CH2:49][CH2:50][NH:51][C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=2)=[O:10])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 860284705-Hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amideYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-hydroxypyridine-2-carboxylic acid (0.103 g, 0.74 mmol) in dichloromethane was added diisopropylethylamine (0.279 mL, 1.6 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.012 g, 0.8 mmol) and EDCI (0.153 g, 0.8 mmol). The resulting mixture was stirred for 15 minutes and 3-phenyl-1-propylamine (0.108 g, 0.8 mmol) was added. After stirring for 22 h, the reaction mixture was diluted with dichloromethane (80 mL), washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by column chromatography afforded 5-hydroxypyridine-2-carboxylic acid (3-phenylpropyl)amide as white crystals (0.116 g, 61% yield). MS (ES+) m/z 257.2 (M+1).

Workup

  1. stirringAfter stirring for 22 h
  2. washwashed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-bf3d8eb995fe4aa99d493440b388b985
Source dataset
uspto-grants-2010_07
Patent number
US07763618B2

Reaction notes

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