HCID 11202234, compound → HCID 11420068, compound

HRID 1270995Notes

Reaction equation

HRID 1270995 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][NH:7][C:8](=[O:35])/[CH:9]=[CH:10]/[C@@H:11]([NH:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:3])[CH3:2]>CCO.[Pd]>[CH:1]([NH:4][CH2:5][CH2:6][NH:7][C:8](=[O:35])[CH2:9][CH2:10][C@@H:11]([NH:19][C:20]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][CH:28]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11202234HCID 11202234, compound

Product 1

HCID 11420068HCID 11420068, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid (2-isopropylamino-ethyl)-amide (Example 21) (0.03 g, 0.06 mmol) in EtOH (0.64 mL) was added Pd/C (10%, 0.011 g). The reaction vessel was sealed, flushed with N2 followed by evacuation (3×), and was then placed under H2 (1 atm), and the contents were stirred at rt for 3 h. The suspension was filtered through diatomaceous earth, which was washed with copious amounts of MeOH. The filtrate was concentrated under reduced pressure to afford 0.03 g (99%) of the desired product as a white solid. MS (electrospray): mass calculated for C29H36N4O2, 472.28; m/z found, 473.3 [M+H]+, 495.2 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.85 (br s, 1H), 7.50–7.09 (m, 14H), 6.84 (br s, 1H), 5.72 (br d, J=7.8 Hz, 1H), 4.12–4.00 (m, 1H), 3.32–3.23 (m, H), 3.20–3.12 (m, 1H), 2.80 (dd, J=13.6, 6.3 Hz, 1H), 2.70–2.56 (m, 5H), 2.20 (br t, J=6.8 Hz, 2H), 1.79–1.72 (m, 1H), 1.69–1.60 (m, 1H), 0.89 (d, J=6.3 Hz, 6H).

Workup

  1. customThe reaction vessel was sealed
  2. customflushed with N2
  3. filtrationThe suspension was filtered through diatomaceous earth, which
  4. washwas washed with copious amounts of MeOH
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc25b7c4d02b4cdebd673bdf545c7009
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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