HCID 90463263, compound → HCID 90460972, compound

HRID 2271409Notes

Reaction equation

HRID 2271409 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:41])[CH2:9][CH2:10][N:11]([CH2:13][C:14]1[C:15]([C:25]2[CH2:30][CH2:29][N:28](C(OCC3C=CC=CC=3)=O)[CH2:27][CH:26]=2)=[N:16][N:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:18]=1)[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[CH3:41][N:8]([CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][C:14]1[C:15]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:16][N:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:18]=1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 90463263HCID 90463263, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90460972HCID 90460972, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(4-(((2-(tert-butoxycarbonyl(methyl)amino)ethyl)(methyl)amino)methyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2 g, 3.52 mmol, 1.00 equiv) and 10% palladium on carbon (2 g) catalyst in methanol (100 mL) was stirred under 1 atmosphere of hydrogen at room temperature for 6 h. The catalyst was removed by filtration and the filtrate was concentrated under vacuum to yield 1.1 g (72%) of (R/S) tert-butyl methyl(2-(methyl-((3-(piperidin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate as a brown oil. 1H-NMR (300 MHz, CDCl3): δ 7.46 (s, 1H), 5.33-5.32 (m, 1H), 4.24-4.06 (m, 1H), 3.75-3.66 (m, 1H), 3.51 (s, 1H), 3.41-3.15 (m, 6H), 2.95-2.70 (m, 6H), 2.62-2.40 (m, 2H), 2.22 (s, 3H), 1.55-1.41 (m, 10H), 1.35-1.21 (m, 1H) ppm. LCMS (method A, ESI): RT=1.49 min, m/z=436.2 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d420d7dc37844b8db5220e2bebbc1be4
Source dataset
uspto-grants-2015_09
Patent number
US09120757B2

Reaction notes

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