Dimethylformamide → HCID 66597480, compound

HRID 1627761Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)=O.Cl[Si](C)(C)C.CN([CH:25]=[O:26])C>>[CH3:5][C:4]1[N:1]=[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][C:4]=3[C:3]2=[C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:3]=1[CH2:10][C:12]([O:26][CH3:25])=[O:13]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 6397Chlorotrimethylsilane

HCID 9813406HCID 9813406, compound

Product 1

HCID 66597480HCID 66597480, compoundYield 62%

Procedure

This compound was prepared according to the procedure B from (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)(furan-2-yl)methanone (0.440 g, 1.886 mmol), methyl levunilate (0.26 mL, 1.886 mmol), chlorotrimethylsilane (0.964 mL, 7.54 mmol) in DMF (3.7 mL) for 18 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (2-50%) in heptane furnished 0.385 g (62%) of the title compound as a yellow solid.

Workup

customThis compound was prepared
customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (2-50%) in heptane

Sources & evidence

ORD record: ord-68912cef6bbd42059962929b0cb60a6a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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