ChemicalBook CAS DataBase List Caspase-3/7 Inhibitor I

Caspase-3/7 Inhibitor I synthesis

7synthesis methods

Product Name:Caspase-3/7 Inhibitor I
CAS Number:220509-74-0
Molecular formula:C14H16N2O5S
Molecular Weight:324.35

63126-47-6 Synthesis

63126-47-6
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132898-96-5 Synthesis

132898-96-5
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220509-74-0
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Yield:220509-74-0 93%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in tetrahydrofuran;chloroform at 0; for 1.5 h;

Steps:

1.2 8-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one

Step 2: 5-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold suspension of 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (5.28 g, 21.5 mmol) in a 1:1 mixture of THF:CHCl₃ (254 mL) was added drop-wise via syringe pump a solution of (S)-(+)-2-(methoxymethyl)-pyrrolidine (3.45 mL, 28.0 mmol, 1.3 eq) (Aldrich) and N,N-diisopropylethylamine (7.49 mL, 43 mmol, 2 eq) in CHCl₃ (42 mL) over a period of 70 minutes under a dry N₂ atmosphere with cooling in an ice bath. After stirring an additional 20 minutes the mixture was concentrated. The residue was flash chromatographed (Biotage KP silica gel, 98/2 CH₂Cl₂/CH₃OH) to give the title compound as a dark greenish-yellow foam (6.48 g. 93% yield). NMR (400 MHz, DMSO-d₆): consistent MS: (API-ES^-) m/z 323[M-H].

References:

US2005/250798,2005,A1 Location in patent:Page/Page column 21

91-56-5 Synthesis