Riboflavin → HCID 59547994, compound

HRID 1946338Notes

Reaction equation

HRID 1946338 reaction equation
CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.[F:28][C:29]1[CH:56]=[CH:55][CH:54]=[C:53]([F:57])[C:30]=1[C:31]([NH:33][C:34]1[CH:38]=[CH:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([N+:46]([O-])=O)[CH:43]=[CH:42][C:41]=2[C:49]([F:52])([F:51])[F:50])[N:35]=1)=[O:32]>[Pd].C(O)C>[NH2:46][C:44]1[CH:43]=[CH:42][C:41]([C:49]([F:51])([F:52])[F:50])=[C:40]([CH2:39][N:36]2[CH:37]=[CH:38][C:34]([NH:33][C:31](=[O:32])[C:30]3[C:29]([F:28])=[CH:56][CH:55]=[CH:54][C:53]=3[F:57])=[N:35]2)[CH:45]=1

Participants

5

Reactant 2

HCID 493570Riboflavin2×HCID 59547920HCID 59547920, compound

Product 1

HCID 59547994HCID 59547994, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To 10% palladium on activated carbon degussa type E101 NE/W (wet) (440 mg, 4.14 mmol, Aldrich) was added a slight suspension of the 2,6-difluoro-N-(1-{[5-nitro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Intermediate 40) (2.0 g, 4.69 mmol) in a solution of ethanol (80 ml) under vacuum. A further amount of 10% palladium on activated carbon degussa type E101 NE/W (wet) (0.2 g) was added after 2 h. The suspension was hydrogenated for a total of 4 h at ambient temperature. The suspension was filtered and the residue washed with ethanol (50 ml). The solvent was removed in vacuo to leave a pale yellow foam (1.79 g); LCMS: (System 4) MH+=397, tRET=2.65 min.

Workup

  1. additionwas added
  2. additionwas added after 2 h
  3. customwas hydrogenated for a total of 4 h at ambient temperature
  4. filtrationThe suspension was filtered
  5. washthe residue washed with ethanol (50 ml)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8aedd85d384b482b8a3f56f1fc1f5ab7
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

Loading…