HCID 59000784, compound → HCID 52942491, compound

HRID 1594017Notes

Reaction equation

HRID 1594017 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:8]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=2)[N:9]2[C:14]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:8]([C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=2)[N:9]2[C:14]=1[C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[N:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 59000784HCID 59000784, compound

Product 1

HCID 52942491HCID 52942491, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

HCO2NH4 (29 mg, 0.459 mmol) was added to a suspension of 9 (50 mg, 0.092 mmol) and 10% Pd/C (10 mg) in EtOH (10 mL). The reaction mixture was stirred at ambient temperature for 24 h. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The resulting residue was triturated in (1:1) Et2O/hexane and the resulting precipitate was collected by vacuum filtration to provide the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 0.84 (t, J=7.1 Hz, 3H), 1.09 (t, J=7.0 Hz, 3H), 3.39 (m, 4H), 3.51 (q, J=7.1 Hz, 2H), 3.67 (m, 4H), 4.07 (q, J=7.2 Hz, 2H), 6.60 (d, J=8.4 Hz, 2H), 6.80 (s, 1H), 7.27 (d, J=8.3 Hz, 2H), 7.44 (m, 5H). Mass Spectrum (ESI+) m/e=515.3 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was triturated in (1:1) Et2O/hexane
  4. filtrationthe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-21ae30a0236d4b25a60e67137f41d8e3
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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