Trimethylsilyl iodide → 5-Chloro-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene-6-carbonitrile

HRID 1013350Notes

Reaction equation

HRID 1013350 reaction equation
C(OC([N:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10]3[C:16]([C:17]#[N:18])=[C:15]([Cl:19])[S:14][C:11]=32)[CH2:7]1)=O)C.I[Si](C)(C)C>C(Cl)Cl>[Cl:19][C:15]1[S:14][C:11]2[CH:12]3[CH:8]([CH2:9][C:10]=2[C:16]=1[C:17]#[N:18])[CH2:7][NH:6][CH2:13]3

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131727022HCID 131727022, compound

Product 1

HCID 116082745-Chloro-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step b) (13.9 mg, 0.047 mmol) was treated with iodotrimethylsilane (10 μl, 0.07 mmol) in CH2Cl2 (235 μl) at 50° C. for 16 hours. The solvent was concentrated and the residue was dissolved in MeOH and purified by preparative LC/MS providing the title compound as a white solid. 1H NMR (300 MHz, CD3OD, ppm) 2.80-2.90 (m, 1H); 3.10-3.50 (m, 5H); 3.55-3.70 (m, 1H); 4.00-4.21 (m, 1H); MS calculated for C10H9ClN2S+H 225, observed 225.

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in MeOH
  3. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-a0a7595b122b4cba9907b73efc0a3543
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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