{2-(4-Chloro-phenyl)-2-[6-(3-methyl-1-trityl-1H-pyrazol-4-yl)-pyridin-3-yl]-vinyl}-methyl-(1-phenyl-ethyl)-amine → HCID 11311982, compound

HRID 1798379Notes

Reaction equation

HRID 1798379 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:21]=[N:22][C:23]([C:26]3[C:27](C)=[N:28][N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:30]=3)=[CH:24][CH:25]=2)=[CH:9][N:10](C)[CH:11](C2C=CC=CC=2)C)=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[CH3:11][NH:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:20]1[CH:21]=[N:22][C:23]([C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 76753191{2-(4-Chloro-phenyl)-2-[6-(3-methyl-1-trityl-1H-pyrazol-4-yl)-pyridin-3-yl]-vinyl}-methyl-(1-phenyl-ethyl)-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 11311982HCID 11311982, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of {2-(4-Chloro-phenyl)-2-[6-(3-methyl-1-trityl-1H-pyrazol-4-yl]-pyridin-3-yl)-vinyl}-methyl-(1-phenyl-ethyl)-amine in ethanol was added palladium, 10 wt. % on activated carbon and the reaction mixture was subjected to a hydrogen atmosphere for 17 hours. The mixture was filtered through Celite®, the mother liquor was concentrated, the residue was purified by column chromatography (SiO2), eluting with dichloromethane: methanol: acetic acid:water (240:20:3:2) to dichloromethane: methanol: acetic acid:water (90:18:3:2) to afford the title compound. LC/MS: (PS-A2) Rt 1.59 [M+H]+ 293.18. 1H NMR (Me-d3-OD) δ 2.35 (3H, s), 2.40 (3H, s), 3.25 (2H, s), 4.15-4.20 (1H, t), 7.10-7.18 (1H, m), 7.25 (4H, m), 7.45 (1H, d), 7.67 (1H, dd), 7.80 (1H, s), 8.38 (1H, s).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe mother liquor was concentrated
  3. customthe residue was purified by column chromatography (SiO2)
  4. washeluting with dichloromethane: methanol: acetic acid:water (240:20:3:2) to dichloromethane: methanol: acetic acid:water (90:18:3:2)

Sources & evidence

ORD record
ord-7ad50fce34ef44e19804bdc83597b0c2
Source dataset
uspto-grants-2013_01
Patent number
US08343953B2

Reaction notes

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