HCID 70154690, compound → HCID 18342546, compound

HRID 2301176Notes

Reaction equation

HRID 2301176 reaction equation
C([O:8][C:9](=[O:45])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[N:17]1[CH2:21][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:19]([CH2:28][N:29]2[CH2:34][CH2:33][CH:32]([N:35]([CH2:42][CH:43]=[CH2:44])[C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[CH2:31][CH2:30]2)[CH2:18]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH2:42]([N:35]([CH:32]1[CH2:33][CH2:34][N:29]([CH2:28][C@@H:19]2[C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][N:17]([C@@H:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]3[CH2:10][C:9]([OH:45])=[O:8])[CH2:18]2)[CH2:30][CH2:31]1)[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)[CH2:43][CH3:44]

Participants

5

Reactant 2

HCID 70154690HCID 70154690, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18342546HCID 18342546, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(R)-(3-(S)-((4-(N-(allyl)-N-(pyrid-3-yl)-amino)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid benzyl ester (37 mg, 0.061 mmol from Step C) in 2 mL MeOH was stirred with 13 mg (0.012 mmol) 10% palladium on carbon under 1 atm of hydrogen using a balloon. After 2 h the mixture was filtered and concentrated to provide 30 mg of the title compound. 1H NMR (500 MHz, CDCl3) δ 0.90-0.93 (t, 3H, J=7.5 Hz), 1.1-3.4 (m, 33H), 6.91-6.93 (d, 1H, J=8 Hz), 7.07-7.1 (m, 1H), 7.2-7.35 (m, 5H), 7.92-7.93 (d, 1H, J=4 Hz), 8.08-8.09 (d, 1H, J=2 Hz). ESI-MS. M/z; (M+H)=519.4 (obs), 519.36 (calc.).

Workup

  1. filtrationAfter 2 h the mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a17bda230e0441d28557f7072f7fc8b4
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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