4-[6-(4-Cyano-phenyl)-2-oxo-3,3-bis-(1-trityl-1H-imidazol-4-ylmethyl)-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide → HCID 178486137, compound

HRID 1355662Notes

Reaction equation

HRID 1355662 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH2:57][C:58]4[N:59]=[CH:60][N:61](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:62]=4)([CH2:32][C:33]4[N:34]=[CH:35][N:36](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:37]=4)[C:14](=[O:31])[N:15]3[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]>C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH2:32][C:33]4[N:34]=[CH:35][NH:36][CH:37]=4)([CH2:57][C:58]4[N:59]=[CH:60][NH:61][CH:62]=4)[C:14](=[O:31])[N:15]3[CH2:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([N:28]([CH3:29])[CH3:30])(=[O:26])=[O:27])=[CH:23][CH:24]=3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 1

HCID 867590514-[6-(4-Cyano-phenyl)-2-oxo-3,3-bis-(1-trityl-1H-imidazol-4-ylmethyl)-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide

Product 1

HCID 178486137HCID 178486137, compoundYield 5.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

4-[6-(4-Cyano-phenyl)-2-oxo-3,3-bis-(1-trityl-1H-imidazol-4-ylmethyl)-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide (0.3 g, 0.4 mmol) was dissolved in a solution of 4.0 ml of TFA and 500 μL of triethylsilane under an atmosphere of dry N2 and stirred for 1 hour. The heterogeneous mixture was concentrated under vacuum and partitioned between aqueous 0.1 N HCl and ethyl ether (Et2O). The water layer was washed with Et2O and then basified to pH˜9 with sodium hydroxide (NaOH). The water layer was then washed 3 times with DCM. The DCM layers were combined and dried over Na2SO4, filtered and concentrated under vacuum to give 13 mg of the titled compound as a purple solid.

Workup

  1. concentrationThe heterogeneous mixture was concentrated under vacuum
  2. custompartitioned between aqueous 0.1 N HCl and ethyl ether (Et2O)
  3. washThe water layer was washed with Et2O
  4. washThe water layer was then washed 3 times with DCM
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3e19f213f7044f70a97b4808587d811d
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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