HCID 68471318, compound → HCID 68467297, compound

HRID 506781Notes

Reaction equation

HRID 506781 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[N:13](C(OC(C)(C)C)=O)[CH:12]=3)=[CH:10][C:3]=12>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:32])=[O:33])[C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[NH:13][CH:12]=3)=[CH:10][C:3]=12

Participants

4

Reactant 1

HCID 68471318HCID 68471318, compound

Product 1

HCID 68467297HCID 68467297, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve bisazaindole 27 (0.28 g, 0.48 mmol) in TFA at 50%/CH2Cl2 (8.0 mL) and stir at room temperature for 5 h. The reaction medium is concentrated under vacuum, and the residue is dissolved in EtOAc (100 mL), washed with saturated NaHCO3 (3×), dried (MgSO4) and concentrated, to give 28 (0.222 g, 96%) as an amorphous solid: TLC (EtOAc at 40%/heptane) Rf=0.05.

Workup

  1. concentrationThe reaction medium is concentrated under vacuum
  2. dissolutionthe residue is dissolved in EtOAc (100 mL)
  3. washwashed with saturated NaHCO3 (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-968ec7ba0d4d432680e4a1b757f836d0
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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