HCID 70874870, compound → HCID 70913555, compound

HRID 2208960Notes

Reaction equation

HRID 2208960 reaction equation
C([N:8]1[C@H:13]([CH3:14])[CH2:12][CH:11]([N:15]([CH2:40][CH3:41])[C:16]2[C:17]([CH3:39])=[C:18]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=2)[C:19]([NH:21][CH2:22][C:23]2[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=2[CH3:29])=[O:20])[CH2:10][C@H:9]1[CH3:42])C1C=CC=CC=1>CO.[Pd]>[CH3:29][C:28]1[CH:27]=[C:26]([CH3:30])[NH:25][C:24](=[O:31])[C:23]=1[CH2:22][NH:21][C:19](=[O:20])[C:18]1[CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=[C:16]([N:15]([CH:11]2[CH2:12][C@@H:13]([CH3:14])[NH:8][C@H:9]([CH3:42])[CH2:10]2)[CH2:40][CH3:41])[C:17]=1[CH3:39]

Participants

4

Reactant 1

HCID 70874870HCID 70874870, compound

Product 1

HCID 70913555HCID 70913555, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-{[(2R,6R)-1-benzyl-2,6-dimethylpiperidin-4-yl](ethyl)amino}-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-2-methyl-5-(trifluoromethyl)benzamide (267 mg, 0.459 mmol) in MeOH (5 mL) was added Pd/C (250 mg). The reaction mixture was stirred at et for 2 hour under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (1. NAM-300H silica gel produced by Nagara Science Co., Ltd., ethylacetate/MeOH=4/1 to ethylacetate/MeOH/triethylamine=1/1/0.01, 2. NH—SiO2, heptane/ethylacetate=30/1 to 8/1) to give the titled compound as a white solid (127 mg, 56% yield). 1H-NMR (400 MHz, CDCl3) δppm; 7.30 (s, 1H), 7.26 (s, 1H), 7.14 (t, J=6.1 Hz, 1H), 5.94 (s, 1H), 4.54 (dd, J=5.9, 1.6 Hz, 2H), 3.41-3.49 (m, 1H), 3.01-3.13 (m, 3H), 2.85-2.92 (m, 1H), 2.40 (s, 3H), 2.32 (s, 3H), 2.22 (s, 3H), 1.63-1.80 (m 4H), 1.13 (d, J=7.0 Hz, 3H), 1.02 (d, J=6.2 Hz, 3H), 0.83 (t, J=7.0 Hz, 3H); LC-MS: m/z [M+H] 493.1, [M+Na] 515.3; HPLC; 97.2% purity.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (1. NAM-300H silica gel produced by Nagara Science Co., Ltd., ethylacetate/MeOH=4/1 to ethylacetate/MeOH/triethylamine=1/1/0.01, 2. NH—SiO2, heptane/ethylacetate=30/1 to 8/1)

Sources & evidence

ORD record
ord-92e60f4ac39f4fa38dbf74d8da2bd71f
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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