HCID 59807059, compound → HCID 59807138, compound

HRID 1922439Notes

Reaction equation

HRID 1922439 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=2)[CH2:17][CH2:16][CH2:15]1)[C:3](=[O:11])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.[Pd]>[NH2:24][C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][CH2:16][CH2:15][N:14]2[CH2:13][CH2:12][N:2]([CH3:1])[C:3](=[O:11])[O:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 59807059HCID 59807059, compound

Product 1

HCID 59807138HCID 59807138, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 2 (1.85 g, 5.205 mmol) in dry ethanol (30 mL) was treated with Pd—C (˜0.2 g) and purged with hydrogen gas. The reaction was stirred at room temperature under hydrogen (balloon pressure) for 3 h. The reaction was filtered through celite bed and washed with methanol (3×20 mL). The combined organic layer was evaporated to obtain crude compound 3 (1.67 g, 99%) as a syrup. ESI-MS (m/z, %): 326 (MH+, 100).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with methanol (3×20 mL)
  4. customThe combined organic layer was evaporated

Sources & evidence

ORD record
ord-ba7732c56dbf4a41903b11ddd63e4208
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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