HCID 59807093, compound → HCID 59807105, compound

HRID 1922423Notes

Reaction equation

HRID 1922423 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]2[N:8]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:23]=[CH:22][C:7]2[N:8]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 59807093HCID 59807093, compound

Product 1

HCID 59807105HCID 59807105, compoundYield 111.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 2 (500 mg, 1.56 mmol) in dry ethanol (10 mL) was treated with Pd—C (˜0.05 g) and purged with hydrogen gas. The reaction mixture was stirred at room temperature under hydrogen atmosphere (balloon pressure) overnight (18 h). The mixture was filtered through a celite bed and washed with methanol (3×25 mL). The combined organic fractions were dried under reduced pressure to obtain crude compound 3 (0.5 g, quantitative) as a colourless foam. 1H-NMR (DMSO-d6) δ 1.34 (m, 6H), 1.87-2.22 (m, 10H), 5.00-5.03 (m, 2H), 6.34-6.52 (m, 2H), 6.98 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %): 288.2 (MH+, 100), 203.1 (37).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe mixture was filtered through a celite bed
  3. washwashed with methanol (3×25 mL)
  4. customThe combined organic fractions were dried under reduced pressure

Sources & evidence

ORD record
ord-a99d3c71d9974db2bec24ecb80bfa3cc
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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