HCID 178508957, compound → HCID 178508955, compound

HRID 2234778Notes

Reaction equation

HRID 2234778 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C:9]1[NH:13][C:12](=[C:14]2[C:27]3[C:26]4[C:21](=[C:22]([N+:28]([O-])=O)[CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]=3[C:18](=[O:31])[NH:17][CH2:16][CH2:15]2)[C:11](=[O:32])[N:10]=1>CO.[Pd]>[NH2:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:21]=1[NH:20][C:19]1[C:18](=[O:31])[NH:17][CH2:16][CH2:15][C:14](=[C:12]3[C:11](=[O:32])[N:10]=[C:9]([NH2:8])[NH:13]3)[C:27]2=1

Participants

4

Reactant 1

HCID 178508957HCID 178508957, compound

Product 1

HCID 178508955HCID 178508955, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(2-amino-5-oxo-3,5-dihydro-imidazol-4-ylidene)-9-nitro-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one TFA salt (4 mg, 8.8 μmol) in MeOH (3 mL) is added 10% Pd/C (10 mg). The mixture is stirred at room temperature under hydrogen atmosphere overnight and then the catalyst is removed by filtration. The solution is concentrated and the residue purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA) to give 9-amino-5-(2-amino-5-oxo-3,5-dihydro-imidazol-4-ylidene)-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one; 1H NMR (MeOD-d4) δ 3.48-3.53 (m, 4H), 7.358 (d, 1H, J=6.0 Hz), 7.362 (d, 1H, J=3.2 Hz), 7.63 (dd, 1H, J1=3.2 Hz, J2=6.0 Hz); m/z [M++1] 311.1.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationThe solution is concentrated
  3. customthe residue purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-a9d4c421d54a4a04b8d7bd98766c503b
Source dataset
uspto-grants-2010_05
Patent number
US07713958B2

Reaction notes

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