1H-1,2,4-Triazole → (4S)-11-[2-(dimethyl-[1,2,4]triazol-1-ylmethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246545Notes

Reaction equation

HRID 2246545 reaction equation
I[CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12.[NH:34]1[CH:38]=[N:37][CH:36]=[N:35]1.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH3:32][Si:3]([CH3:33])([CH2:2][N:34]1[CH:38]=[N:37][CH:36]=[N:35]1)[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 516892Sodium BicarbonateHCID 5765938311-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Product 1

HCID 25261403(4S)-11-[2-(dimethyl-[1,2,4]triazol-1-ylmethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dioneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 4 (60 mg), 1,2,4-triazole (22 mg) and NaHCO3 (26 mg) in dry N,N-dimethylformamide (1 mL) was heated at 70° C. for 5 hours under argon. The N,N-dimethylformamide was removed from the reaction mixture under vacuum and the residue was directly eluted on a silica gel column using 4% ethanol in dichloromethane to obtain the required product in 79% yield (43 mg).

Workup

  1. customThe N,N-dimethylformamide was removed from the reaction mixture under vacuum
  2. washthe residue was directly eluted on a silica gel column

Sources & evidence

ORD record
ord-58c3d926ead8472c877cd9b357ba3624
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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