Acetic Anhydride → N-(2-{5-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-cyano-phenoxy}-ethyl)-acetamide

HRID 1585914Notes

Reaction equation

HRID 1585914 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[C:11]([CH2:13][N:14]2[C:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]4=[O:33])=[N:24][CH:25]=3)=[CH:17][N:16]=[CH:15]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[C:34](OC(=O)C)(=[O:36])[CH3:35].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:32][C:30]1[CH:29]=[CH:28][C:27](=[O:33])[N:26]([C:23]2[CH:22]=[CH:21][C:20]([CH2:19][C:18]3[N:14]([CH2:13][C:11]4[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([CH:12]=4)[O:4][CH2:3][CH2:2][NH:1][C:34](=[O:36])[CH3:35])[CH:15]=[N:16][CH:17]=3)=[CH:25][N:24]=2)[CH:31]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 187797582-(2-Amino-ethoxy)-4-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile

Product 1

HCID 18779795N-(2-{5-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-cyano-phenoxy}-ethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Amino-ethoxy)-4-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile (L-824,459, 50 mg, 0.11 mmol) was dissolved in CH2Cl2 (550 tl) and treated with acetic anhydride (208 μl, 0.22 mmol). DIEA was then added until pH=7-8. The reaction mixture was stirred at room temp. for 2 hours. Saturated NaHCO3 was added (10 mL) and the solution was extracted with CH2Cl2 (2×10 mL). The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to yield the final product.

Workup

  1. extractionthe solution was extracted with CH2Cl2 (2×10 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-95f52a52d11c4f4e9311ba5a52028018
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

Loading…