HCID 58046742, compound → HCID 58046623, compound

HRID 2362880Notes

Reaction equation

HRID 2362880 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[NH:17][C:16]3=[O:24])[CH2:8][CH2:7]2)[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4][N:3]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38]CC1C=CC=CC=1)=[O:37]>[Pd].C(OCC)(=O)C.CO>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[NH:17][C:16]3=[O:24])[CH2:10][CH2:11]2)[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4][N:3]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37]

Participants

4

Reactant 1

HCID 58046742HCID 58046742, compound

Product 1

HCID 58046623HCID 58046623, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of benzyl 6-(4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)hexanoate (0.25 g, 0.41 mmol) in 4:1 ratio of ethyl acetate/methanol (4 mL), was added 10 wt % palladium on carbon (0.1 g). After stirring under hydrogen at room temperature and atmospheric pressure for 2 hours, the reaction mixture was filtered, washed with 1% acetic acid in methanol, concentrated in vacuo and isolated by reverse phase HPLC to obtain the title compound (0.09 g, 42%); 1H NMR (DMSO-d6): δ 1.21-1.26 (m, 2H), 1.47-1.57 (m, 6H), 1.77-1.82 (m, 2H), 2.18 (t, 2H, J=7.2 Hz), 2.32 (t, 2H, J=6.4 Hz), 2.59-2.67 (m, 6H), 2.91 (d, 2H, J=11.2 Hz), 3.84 (t, 2H, J=6.4 Hz), 4.64 (s, 2H), 6.76 (t, 1H, J=7.2 Hz), 6.88 (d, 2H, J=8.4 Hz), 6.96 (d, 3H, J=3.6 Hz), 7.18-7.20 (m, 1H), 7.24 (t, 2H, J=8.8 Hz), 10.82 (s, 1H); MS for C29H37N5O4 m/z 520.08 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with 1% acetic acid in methanol
  3. concentrationconcentrated in vacuo
  4. customisolated by reverse phase HPLC

Sources & evidence

ORD record
ord-89d268930eb0449c87dbd2db86e7f75b
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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