HCID 59807139, compound → HCID 59807149, compound

HRID 1922404Notes

Reaction equation

HRID 1922404 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[NH:10][C:9]2=[O:20])[CH2:4][CH2:3]1>C(O)C.[Pd]>[NH2:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:20])[CH:8]2[CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 59807139HCID 59807139, compound

Product 1

HCID 59807149HCID 59807149, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 2 (0.18 g, 0.654 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.02 g) and purged with hydrogen gas. The reaction was stirred at room temperature under hydrogen atm. (balloon pressure) overnight (16 h). The reaction was filtered through celite bed, washed with methanol (3×10 mL). The combined organic layer was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 3 (0.08 g, 50%) as a foam. 1H NMR (DMSO-d6) δ 9.89 (s, 1H), 6.57 (s, 1H), 6.48 (d, 1H, J=8.1 Hz), 6.37 (d, 1H, J=8.1 Hz), 4.64 (s, 2H), 2.78-2.67 (m, 2H), 2.09-2.04 (m, 4H), 1.87-1.70 (m, 3H), 1.61-1.52 (m, 2H), 1.37-1.26 (m, 2H); ESI-MS (m/z, %): 246 (MH+, 100).

Workup

  1. custompurged with hydrogen gas
  2. custom(balloon pressure) overnight (16 h)
  3. filtrationThe reaction was filtered through celite bed
  4. washwashed with methanol (3×10 mL)
  5. customThe combined organic layer was evaporated
  6. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-835764b3095c47429707b00226130042
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…