Triethylamine → HCID 86611069, compound

HRID 1877927Notes

Reaction equation

HRID 1877927 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=1[Cl:21])[N:5]1[C:9]([CH2:10][CH2:11][OH:12])=[CH:8][N:7]=[CH:6]1.CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=1[Cl:21])[N:5]1[C:9]([CH2:10][CH2:11][O:12][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66885929HCID 66885929, compound

Product 1

HCID 86611069HCID 86611069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude (2-chloro-4-cyanophenyl)-[5-(2-hydroxyethyl)imidazol-1-yl]acetic acid methyl ester (2.06 g, 6.46 mmol) is dissolved in CH2Cl2 (25 mL) and stirred at 0° C. before Et3N (1.4 mL, 9.69 mmol) and methanesulfonyl chloride (0.6 mL, 7.75 mmol) are added. After completion of the reaction, the solution is partitioned between CH2Cl2 and aqueous saturated NaHCO3. The organic layer is dried (Na2SO4) and evaporated to give the crude (2-chloro-4-cyanophenyl)-[5-(2-methanesulfonyloxyethyl)imidazol-1-yl]-acetic acid methyl ester that is used without further purification. MS (ESI) m/z 398.2, 400.2 (M+H).

Workup

  1. additionare added
  2. customAfter completion of the reaction
  3. customthe solution is partitioned between CH2Cl2 and aqueous saturated NaHCO3
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-54bf2584ab124e5b848df0ba9bcfa212
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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