HCID 86758722, compound → HCID 18342549, compound

HRID 2301180Notes

Reaction equation

HRID 2301180 reaction equation
[CH2:1]([N:4]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]2[C@@H:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:21][N:20]([C@@H:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]3[CH2:35][C:36]([O:38]CC3C=CC=CC=3)=[O:37])[CH2:19]2)[CH2:13][CH2:12]1)[C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:2][CH3:3].[H][H]>CO.[Pd]>[CH2:1]([N:4]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]2[C@@H:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:21][N:20]([C@@H:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]3[CH2:35][C:36]([OH:38])=[O:37])[CH2:19]2)[CH2:13][CH2:12]1)[C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 86758722HCID 86758722, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18342549HCID 18342549, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(R)-(3-(S)-((4-(N-(prop-1-yl)-N-(pyrimid-2-yl)amino)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexylacetic acid, benzyl ester (0.026 ml, 0.24 mmol) from Step A), in 3.0 mL of MeOH was hydrogenated using 10% palladium on carbon (28 mg, 0.026 mmol) under one atmosphere of hydrogen gas. After TLC indicated the absence of the starting benzylester, the reaction was filtered through a 0.45 micron nylon membrane polypropylene filter and concentrated under reduced pressure to give 50 mg (74%) of the title compound as a white solid. HPLC (Zorbax SB-C8 column, 4.6 mm×7.5 cm, Gradient: 90 H2O:10 CH3CN to 0 H2O:100 CH3CN over 7.5 minutes then hold at 100 CH3CN:0 H2O for 45 seconds, 2.25 mL/min, 220 nm): Retention Time: 3.28 minutes. ESI-MS: 520 (M+1).

Workup

  1. filtrationthe reaction was filtered through a 0.45 micron nylon membrane polypropylene
  2. filtrationfilter
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f179f67c709d4205bdbec3e2dd0945a4
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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