HCID 54289374, compound → HCID 86758472, compound

HRID 365854Notes

Reaction equation

HRID 365854 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]([CH2:7][CH2:8][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 86758472HCID 86758472, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of 5-(2-(4-pyridinyl)ethenyl)-6-chloro-3-(1-methyl-2-(R)-pyrrolidinylmethoxy)pyridine from Example 82 (85 mg) was dissolved in MeOH. 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 CH2Cl2 :MeOH 100:3-100:10 to afford to give the free base of the title compound (30 mg). MS (CI/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, lH), 3.90 (m, 2H), 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 Et2O to give the title compound. mp 236-238° C. MS (CI/NH3) m/z 332 (M+H)+. 1H NMR (D2O, 300 MHz) δ1.98-2.23 (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 CH2Cl2 :MeOH 100:3-100:10
  5. customto afford

Sources & evidence

ORD record
ord-453e29acc73c4b388c528654eeb3f94f
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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