Imidazole → 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester

HRID 1760410Notes

Reaction equation

HRID 1760410 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:2].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15](S(C)(=O)=O)[N:14]=1.C(N(C(C)C)CC)(C)C.[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1>CS(C)=O>[C:1]([CH2:3][CH2:4][N:5]([C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[N:14]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 521172N-(2-Cyanoethyl)glycine ethyl esterHCID 123976724-Chloro-2-methanesulfonyl-6-methylpyrimidine

Product 1

HCID 865863382-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl esterYield 34.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To N-cyanoethylglycine, ethyl ester (15.9 g, 102 mmol) (a compound of formula (Y2)) dissolved in DMSO (70 mL) was added 4-chloro-6-methyl-2-methylsulfonylpyrimidine (18.8 g, 91 mmol) (a compound of formula (Y1)) and diisopropylethylamine (18 mL, 100 mmol). After stirring for 16 hours, the reaction temperature was raised to 70° C. and imidazole (26.5 g, 0.39 mol) was added. After stirring for 1 day, the reaction was cooled to ambient temperature and added to ice water. The solid that formed was suction filtered and collected on paper to give 9.9 g of 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester (a compound of formula (Yc1)).

Workup

  1. stirringAfter stirring for 1 day
  2. temperaturethe reaction was cooled to ambient temperature
  3. customThe solid that formed
  4. filtrationfiltered
  5. customcollected on paper

Sources & evidence

ORD record
ord-bbb82f6b0b7d47c1ae1edd65bdac1c76
Source dataset
uspto-grants-2005_01
Patent number
US06841674B2

Reaction notes

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