HCID 58285292, compound → HCID 25256267, compound

HRID 1893151Notes

Reaction equation

HRID 1893151 reaction equation
[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([NH:11][CH:12]=[N:13]3)=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]CC4C=CC=CC=4)[CH:17]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO.C1COCC1.[Pd]>[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([NH:11][CH:12]=[N:13]3)=[C:9]([C:16]3[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=3)[N:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 58285292HCID 58285292, compound

Product 1

HCID 25256267HCID 25256267, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound A (45 mg, 0.116 mmol) in methanol (10 mL) and THF (10 mL) was added 50 mg of 10% Pd/C. The mixture was degassed for three times with N2, and hydrogenated under H2 atmosphere over night. After removing Pd/C by filtration, the reaction was evaporated and the residue purified by prep-TLC (PE:EA=1:2) to give 1 (26 mg, 75%). 1H-NMR (300 MHz, DMSO-d6): δ=3.73-3.76 (m, 8H), 6.89-6.92 (m, 1H), 7.30-7.35 (m, 1H), 8.19 (s, 1H), 8.23 (m, 2H), 9.59 (s, 1H). LC-MS [M+H]+: 298.0.

Workup

  1. customThe mixture was degassed for three times with N2
  2. waithydrogenated under H2 atmosphere over night
  3. customAfter removing Pd/C
  4. filtrationby filtration
  5. customthe reaction was evaporated
  6. customthe residue purified by prep-TLC (PE:EA=1:2)

Sources & evidence

ORD record
ord-c247d50467c841a08dbc4be2a733979e
Source dataset
uspto-grants-2013_08
Patent number
US08513221B2

Reaction notes

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