Triacetoxyperiodinane → HCID 49869008, compound

HRID 570955Notes

Reaction equation

HRID 570955 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][N:24]1[C:29](=[O:30])[N:28]2[CH:31]=[N:32][C:33]([C:34](=[S:42])[NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:27]2[N:26]=[N:25]1>C(Cl)(Cl)Cl>[S:42]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[N:35]=[C:34]1[C:33]1[N:32]=[CH:31][N:28]2[C:29](=[O:30])[N:24]([CH3:23])[N:25]=[N:26][C:27]=12

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 86663792HCID 86663792, compound

Product 1

HCID 49869008HCID 49869008, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dess Martin periodinane (202 mg, 0.477 mmol) was added in small portions to a solution of 3-methyl-4-oxo-N-phenyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide (300 mg (as 3:2 mixture with carboxamide), 0.434 mmol) in chloroform (60 mL) and the reaction was monitored by thin layer chromatography. The mixture was stirred for 1 hour and 20 mg of Dess Martin periodinane was added. The mixture was stirred for 30 minutes and the crude product was absorbed on silica and purified by flash chromatography using DCM:MeOH (98:2) as eluent to give the pure title compound as a bright yellow solid (12 mg, 10%). δH (DMSO d6): 8.96 (1H, s), 8.20 (1H, d, J=8.0), 8.15 (1H, d, J=8.0), 7.58 (1H, td, J=7.6, 1.3), 7.50 (1H, td, J=7.6, 1.2), 3.90 (3H, s).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customthe crude product was absorbed on silica
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-dc7084db215c40cc9243dd28946a8a02
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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