Riboflavin → N-{1-[(5-amino-2-methylphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

HRID 1946346Notes

Reaction equation

HRID 1946346 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:53]=[CH:52][CH:51]=[C:50]([F:54])[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[CH3:49])[N:35]=1)=[O:32]>[Pd].C(OCC)(=O)C.C(O)C>[NH2:46][C:44]1[CH:43]=[CH:42][C:41]([CH3:49])=[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:53][CH:52]=[CH:51][C:50]=3[F:54])=[N:35]2)[CH:45]=1

Participants

6

Reactant 2

HCID 493570RiboflavinHCID 595480222,6-difluoro-N-{1-[(2-methyl-5-nitrophenyl)methyl]-1H-pyrazol-3-yl}benzamide

Product 1

HCID 59548012N-{1-[(5-amino-2-methylphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10% palladium on activated carbon degussa type E101 NE/W (wet) (280 mg) was added a slight suspension of 2,6-difluoro-N-{1-[(2-methyl-5-nitrophenyl)methyl]-1H-pyrazol-3-yl}benzamide (for a preparation see Intermediate 47)(1.27 g, 3.41 mmol) in a mixture of ethyl acetate (20 ml) and ethanol (50 ml) under vacuum. The suspension was hydrogenated for 1.5 h at ambient temperature. The suspension was filtered and the residue washed with methanol (30 ml). The solvent was removed in vacuo to leave a white solid (1.09 g); LCMS (System 4) MH+=343, tRET=1.43 min.

Workup

  1. additionwas added
  2. filtrationThe suspension was filtered
  3. washthe residue washed with methanol (30 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-681fdccb60344764a644b742ada51c20
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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