Triethylamine → Methyl 6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoate

HRID 1938508Notes

Reaction equation

HRID 1938508 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:11](=[O:12])[N:10]3[C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=[C:9]3[C:6]2=[N:7][CH:8]=1)[CH3:2].Cl.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(N(CC)CC)C>CN(C)C=O>[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([C:9]2[NH:10][C:13](=[O:20])[C:14]([CH:17]([CH3:18])[CH3:19])([CH3:16])[N:15]=2)=[C:5]([CH:4]=1)[C:11]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:12])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 137307167-ethyl-2-isopropyl-2-methyl-5H-imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine-3(2H),5-dione

Product 1

HCID 22450188Methyl 6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoateYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 7-ethyl-2-isopropyl-2-methyl-5H-imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine-3(2H),5-dione (7.25 g, 26.75 mmol) in anhydrous N,N-dimethylformamide is treated successively with methyl 6-aminocaproate hydrochloride (5.10 g, 28.1 mmol) and triethylamine (3.00 g, 29.6 mmol). The resulting mixture is stirred at room temperature under nitrogen for 20.5 hours. After this period, the reaction mixture is partitioned between water and ethyl acetate. The layers are separated, and the organic layer is washed with water, dried over magnesium sulfate and vacuum filtered through diatomaceous earth. The filtrate is concentrated in vacuo to obtain a white solid. The solid is triturated with 1:1 ether/petroleum ether to give the title product as a white solid (7.40 g, 69%, mp 101°-103° C.).

Workup

  1. waitAfter this period
  2. customthe reaction mixture is partitioned between water and ethyl acetate
  3. customThe layers are separated
  4. washthe organic layer is washed with water
  5. dry with materialdried over magnesium sulfate and vacuum
  6. filtrationfiltered through diatomaceous earth
  7. concentrationThe filtrate is concentrated in vacuo
  8. customto obtain a white solid
  9. customThe solid is triturated with 1:1 ether/petroleum ether

Sources & evidence

ORD record
ord-1882b5e0ebdc4ce99cf456aa1daab413
Source dataset
uspto-grants-1997_12
Patent number
US05693658

Reaction notes

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