HCID 86689046, compound → (1R,3R)-3-(4-(4-chloro-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-1-yl)cyclohexanecarboxamide

HRID 75130Notes

Reaction equation

HRID 75130 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:19][CH2:18][CH2:17][CH:16]([C:20]([NH2:22])=[O:21])[CH2:15]3)[CH2:10][CH:9]=2)=[CH:4][C:3]=1[NH:23][C@@H:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])[CH3:25]>[Pd].C(O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C@@H:14]3[CH2:19][CH2:18][CH2:17][C@@H:16]([C:20]([NH2:22])=[O:21])[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:23][C@@H:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])[CH3:25]

Participants

5

Reactant 1

HCID 86689046HCID 86689046, compound

Product 1

HCID 86689045(1R,3R)-3-(4-(4-chloro-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-1-yl)cyclohexanecarboxamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of the 3-(4-(4-chloro-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)-5,6-dihydropyridin-1(2H)-yl)cyclohexanecarboxamide (0.154 g, 0.20 mmol), palladium on carbon (Pd/C) (10% by weight, 0.05 g) in ethanol (7 mL) containing concentrated hydrochloric acid (4 drops) in a Paar shaker flask was hydrogenated at 25 psi for 1 h. The reaction mixture was diluted with ethanol, and filtered through Celite. The filtrate was concentrated in vacuo, and the resulting residue was purified by flash chromatography (SiO2, 5% triethylamine in ethyl acetate) to separate the desired isomer as a white solid (0.038 g, 0.075 mmol, 25%). 1H NMR (400 MHz, CD3OD) δ 7.45-7.41 (m, 2H), 7.26 (dd, J=2.0, 8.4 Hz, 1H), 7.21 (d, J=8.0 Hz, 1H), 6.57 (d, J=8.0 Hz, 1H), 6.21 (s, 1H), 4.99 (dd, J=6.8, 13.2 Hz, 1H), 3.76-3.71 (m, 1H), 3.53-3.52 (m, 3H), 3.20-3.12 (m, 2H), 2.99-2.93 (m, 1H), 2.71-2.65 (m, 1H), 2.47 (d, J=11.6 Hz, 1H), 2.35 (d, J=13.2 Hz, 1H), 2.18-2.10 (m, 2H), 1.99-1.82 (m, 6H), 1.68-1.74 (m, 1H), 1.64-1.51 (m, 6H); MS: (ES) m/z calculated for C26H33Cl3N3O [M+H]+508.2. found 508.4.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by flash chromatography (SiO2, 5% triethylamine in ethyl acetate)

Sources & evidence

ORD record
ord-9fc1618a703d4d1786877c57594833d4
Source dataset
uspto-grants-2014_09
Patent number
US08835419B2

Reaction notes

Loading…