Diisopropylethylamine → [4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-acetic acid methyl ester

HRID 1297582Notes

Reaction equation

HRID 1297582 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([O:33][C:34]3[N:42]=[CH:41][CH:40]=[CH:39][C:35]=3[C:36]([OH:38])=O)=[CH:32][C:27]=2[O:26][CH2:25]1.C(N(CC)C(C)C)(C)C.[CH3:52][O:53][C:54](=[O:64])[CH2:55][C:56]1[CH:61]=[CH:60][C:59]([CH2:62][NH2:63])=[CH:58][CH:57]=1>ClCCl.O>[CH3:52][O:53][C:54](=[O:64])[CH2:55][C:56]1[CH:61]=[CH:60][C:59]([CH2:62][NH:63][C:36]([C:35]2[C:34]([O:33][C:31]3[CH:30]=[CH:29][C:28]4[O:24][CH2:25][O:26][C:27]=4[CH:32]=3)=[N:42][CH:41]=[CH:40][CH:39]=2)=[O:38])=[CH:58][CH:57]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1514145Methyl 4-aminomethylphenylacetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27368792-(1,3-Benzodioxol-5-yloxy)pyridine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 10202284[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.71 g), 1-hydoxybenzo-triazole hydrate (1.24 g), and 2-(benzo[1,3]dioxol-5-yloxy)-nicotinic acid were combined and suspended in anhydrous dichloromethane (40 mL). N,N-diisopropylethylamine (5.93 mL) was added to the suspension, which was stirred for 0.5 h. The suspension was added to (4-aminomethyl-phenyl)-acetic acid methyl ester (1.22 g) and the reaction mixture stirred at ambient temperature overnight. Water (approx. 15 mL) was then added to the reaction mixture, and it was extracted with dichloromethane (7×30 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (ethyl acetate:hexanes=3:2) to yield the title compound (1.41 g).

Workup

  1. stirringthe reaction mixture stirred at ambient temperature overnight
  2. extractionwas extracted with dichloromethane (7×30 mL)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (ethyl acetate:hexanes=3:2)

Sources & evidence

ORD record
ord-2fb9f61ea113439fbf08775257eedea3
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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