HCID 14392657, compound → HCID 14392652, compound

HRID 358596Notes

Reaction equation

HRID 358596 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](/[CH:17]=[CH:18]/[S:19]([NH2:22])(=[O:21])=[O:20])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1>Cl.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][S:19]([NH2:22])(=[O:20])=[O:21])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 14392657HCID 14392657, compound

Product 1

HCID 14392652HCID 14392652, compoundYield 24.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent2×

Procedure

A mixture of the product of stage (i) (0.8 g) in ethanolic hydrogen chloride (80 ml) was hydrogenated over pre-reduced 10% palladium on carbon (50% paste with water, 0.8 g) until uptake ceased. The catalyst was filtered off, washed with hot ethanol (50 ml) and the filtrate evaporated in vacuo to give crude material (0.15 g). The catalyst residues were then warmed (70°) with 2N hydrochloric acid (200 ml), filtered and the filtrate evaporated to dryness in vacuo (azeotroped with toluene). The residue was combined with the crude product obtained above and purified by flash chromatography (silica 9385, 100 g) eluting with CH2Cl2 /EtOH/NH3 (50:8:1) to give the title compound as a solid (0.2 g) m.p. >95° (foams),

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with hot ethanol (50 ml)
  3. customthe filtrate evaporated in vacuo
  4. customto give crude material (0.15 g)
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness in vacuo (azeotroped with toluene)
  7. customobtained above and
  8. custompurified by flash chromatography (silica 9385, 100 g)
  9. washeluting with CH2Cl2 /EtOH/NH3 (50:8:1)

Sources & evidence

ORD record
ord-62ed8e1681664078b853771705d88873
Source dataset
uspto-grants-1991_03
Patent number
US04997841

Reaction notes

Loading…