HCID 19597257, compound → HCID 19597260, compound

HRID 611488Notes

Reaction equation

HRID 611488 reaction equation
C([O:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=2)[N:12]=[C:11]([NH:35][NH:36][C:37](=[O:47])[CH2:38][P:39]([O:44][CH2:45][CH3:46])([O:41][CH2:42][CH3:43])=[O:40])[C:10]1=[O:48])C1C=CC=CC=1>[Pd].C(O)C>[CH2:45]([O:44][P:39]([CH2:38][C:37]([NH:36][NH:35][C:11]1[C:10](=[O:48])[N:9]([OH:8])[C:18]2[C:13]([N:12]=1)=[CH:14][C:15]([N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[C:16]([C:19]([F:21])([F:22])[F:20])[CH:17]=2)=[O:47])([O:41][CH2:42][CH3:43])=[O:40])[CH3:46]

Participants

4

Reactant 1

HCID 19597257HCID 19597257, compound

Product 1

HCID 19597260HCID 19597260, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-benzyloxy-3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-6-(4-methyl-2-phenyl-1H-imidazol-1-yl)-7-trifluoromethylquinoxalin-2(1H)-one (1.8 g, 2.6 mmol) and 50 mg of 5% palladium on carbon in 50 ml of ethanol was hydrogenated at room temperature and atmospheric pressure for 9 h. The catalyst was removed by filtration, the filtrate evaporated to dryness in vacuo and the residue finally triturated with ether to give 1.51 g (97%) of the title compound. M.p.>177° C. decomp. 1H-NMR (DMSO-d6): δ 1.10-1.22 (m, 6H), 2.23 (s, 3H), 2.98 (d, 2H), 4.00 (quint., 4H), 7.12 (s, 1H), 7.18-7.30 (m, 5H), 7.31 (s, 1H), 7.92 (s, 1H), 10.24 (s, 2H), 12.52 (br. s, 1H).

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated to dryness in vacuo
  4. customthe residue finally triturated with ether

Sources & evidence

ORD record
ord-7f469b6d0914437ea53c3bdb0e2b77b8
Source dataset
uspto-grants-1999_12
Patent number
US06001832

Reaction notes

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