Chlorotrimethylsilane → HCID 66597284, compound

HRID 1627773Notes

Reaction equation

HRID 1627773 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)=O.[C:21]([O:28][CH3:29])(=[O:27])[CH2:22][CH2:23][C:24]([CH3:26])=O.Cl[Si](C)(C)C>CN(C=O)C>[CH3:29][O:28][C:21](=[O:27])[CH2:22][C:23]1[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)=[C:3]2[C:4]3[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]2=[N:1][C:24]=1[CH3:26]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 69354Methyl levulinateHCID 28337456HCID 28337456, compound

Product 1

HCID 66597284HCID 66597284, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure B from (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(4-ethylphenyl)methanone (0.471 g; 1.65 mmol), methyl levulinate (0.233 mL; 1.81 mmol), chlorotrimethylsilane (0.845 mL; 6.6 mmol) in DMF (6.6 mL) for 48 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.463 g (74%) of the title compound as a yellow solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane

Sources & evidence

ORD record
ord-1c366e5bdd284d79823bbb4ae1e3b285
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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