Chlorotrimethylsilane → HCID 66597422, compound

HRID 1627774Notes

Reaction equation

HRID 1627774 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:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=O.[C:19]([O:26][CH3:27])(=[O:25])[CH2:20][CH2:21][C:22]([CH3:24])=O.Cl[Si](C)(C)C>CN(C=O)C>[CH3:27][O:26][C:19](=[O:25])[CH2:20][C:21]1[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=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:22]=1[CH3:24]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 69354Methyl levulinateHCID 66603691HCID 66603691, compound

Product 1

HCID 66597422HCID 66597422, compoundYield 39.1%

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)(pyridin-3-yl)methanone (0.362 g; 1.4 mmol), methyl levulinate (0.198 mL; 1.54 mmol), chlorotrimethylsilane (0.717 mL; 5.6 mmol) in DMF (5.6 mL) for 48 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.193 g (39%) 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-c9d47beecbe347798473f45022602e9f
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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