HCID 54289374, compound → HCID 86750813, compound

HRID 1780356Notes

Reaction equation

HRID 1780356 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([O:16][CH2:17][C@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH3:23])[CH:12]=[N:13][C:14]=2[Cl:15])=[CH:3][CH:2]=1>CO.[Pd]>[ClH:15].[ClH:15].[ClH:15].[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([O:16][CH2:17][C@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH3:23])[CH:12]=[N:13][C:14]=2[Cl:15])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 54289374HCID 54289374, compound

Product 1

HCID 86750813HCID 86750813, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of 5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-methyl-2-(R)-pyrrolidinylmethoxy)pyridine from Example 82 (85 mg) was dissolved in methanol. To this solution was added Pd/C (9.5 mg), and the mixture was stirred under H2 for 16 hours at room temperature. The catalyst was filtered off, and the solvent was removed under vacuum. The residue was chromatographed on a silica gel column, eluting with methylene chloride:methanol 100:3-100:10 to afford to give the free base of the title compound (30 mg). MS (DCI/NH3) m/z 332 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.65 (m, 2H), 1.80 (m, 1H), 2.0 (m, 1H), 2.32 (m, 1H), 2.47 (s, 3H), 2.64 (m, 1H), 2.96 (m, 4H), 3.12 (m, 1H), 3.90 (m, 3H), 6.98 (m, 1H), 7.12 (m, 2H), 7.96 (m, 1H), 8.50 (m, 2H). The base was converted to the salt by treatment with HCl in ether to give the title compound. mp 236°-238° C. MS (DCI/NH3) m/z 332 (M+H)+. 1 H NMR (D2O, 300 MHz) δ: 1.98-2.23 (m, 3H), 2.38 (m, 1H), 3.01 (s, 3H), 3.17 (m, 2H), 3.25 (m, 3H), 3.74 (m, 1H), 3.90 (m, 1H), 4.27 (dd, J=7.1, 11.2, 1H), 4.44 (dd, J=3.10, 11.2, 1H), 7.36 (d, J=3.0, 1H), 7.70 (d, J=8.4, 2H), 8.01 (d, J=3.0, 1H), 8.56 (d, J=6.1, 2H). Anal. Calcd for C18H22N3OCl·3 HCl: C, 49.00; H, 5.71; N, 9.52. Found: C, 48.94; H, 5.85; N, 9.23. [α]25D =+8.64° (c 0.94, MeOH).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under vacuum
  3. customThe residue was chromatographed on a silica gel column
  4. washeluting with methylene chloride:methanol 100:3-100:10
  5. customto afford

Sources & evidence

ORD record
ord-dac9ce5b25fc4760a9c1dc2b8718187d
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

Loading…