Ethyl Acetate → HCID 178449954, compound

HRID 1268907Notes

Reaction equation

HRID 1268907 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[NH:7][C:8]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)[N:10]=1)([CH3:5])[CH3:4].[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(OCC)(=O)C>ClCCl>[CH3:4][C:3]([C:6]1[NH:10][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)=[C:8]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[N:7]=1)([CH3:5])[CH2:2][NH:1][S:28]([CH3:27])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 184469145-[2-(2-Amino-1,1-dimethyl-ethyl)-5-pyridin-4-yl-1H-imidazol-4-yl]-indan-1-one

Product 1

HCID 178449954HCID 178449954, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 1, Step 6 (0.1 g, 0.29 mmol) and methane sulphonyl chloride (0.023 ml, 0.3 mmol) in dichloromethane (3 ml) was stirred at room temperature for 2 hours. The reaction was then poured into ethyl acetate, washed with water and aqueous sodium hydrogen carbonate solution, dried (MgSO4) and concentrated in vacuo. The crude residue was then purified by silica gel chromatography eluting with a 1:9:90 mixture of 0.88 ammonia solution:methanol:dichloromethane to give the title compound (0.075 g, 61%) as a yellow solid; MS(AP+) m/e 425 [M+H]+.

Workup

  1. washwashed with water and aqueous sodium hydrogen carbonate solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was then purified by silica gel chromatography
  5. washeluting with a 1:9:90 mixture of 0.88 ammonia solution

Sources & evidence

ORD record
ord-2b52205fbad04097a3774891872b1814
Source dataset
uspto-grants-2007_04
Patent number
US07199137B2

Reaction notes

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