HCID 59316974, compound → HCID 59316982, compound

HRID 1189932Notes

Reaction equation

HRID 1189932 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5](=[O:24])[NH:6][C:7]1[CH:8]=[C:9]([C:13]#[C:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH3:3]>CCO.[Pd]>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:24])[NH:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:10]=[CH:11][CH:12]=1)[CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 59316974HCID 59316974, compound

Product 1

HCID 59316982HCID 59316982, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 3-(3-(3,3-dipropylureido)phenyl)prop-2-ynylcarbamate (25) (0.17 g, 0.455 mmol) in EtOH (10 mL) was degassed with vacuum/Ar. Pd/C (10%, 0.0293 g) was added and the atmosphere was purged with H2. The mixture was stirred under H2-filled balloon at room temperature for 5 hrs. The reaction mixture was filtered through Celite and concentrated under reduced pressure. The residue was crystallized from EtOAc/hexanes to give tert-butyl 3-(3-(3,3-dipropylureido)phenyl)propylcarbamate (26) as a pale yellow solid. Yield (0.0946 g, 55%); 1H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.22-7.26 (m, 2H), 7.07 (t, J=7.6 Hz, 1H), 6.82 (br.t, J=5.1 Hz, 1H), 6.70-6.74 (m, 1H), 3.21 (t, J=7.4 Hz, 4H), 2.90 (q, J=6.1 Hz, 2H), 2.45 (t, J=8.0 Hz, 2H), 1.61 (m, 2H), 1.48 (sextet, J=7.4 Hz, 4H), 1.35 (s, 9H), 0.82 (t, J=7.4 Hz, 6H).

Workup

  1. customthe atmosphere was purged with H2
  2. additionfilled balloon at room temperature for 5 hrs
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-27ca24f12fdd4d9f881a906587d867d1
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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