HCID 178508957, compound → HCID 178508955, compound

HRID 29794Notes

Reaction equation

HRID 29794 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-c25efc0fc2e44314928fec664d655612
Source dataset
uspto-grants-2008_09
Patent number
US07423031B2

Reaction notes

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