HCID 21345251, compound → HCID 21345252, compound

HRID 367091Notes

Reaction equation

HRID 367091 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([O:9][CH2:10][C@H:11]2[CH2:14][CH2:13][N:12]2C(OCC2C=CC=CC=2)=O)=[CH:5][CH:4]=1>CCO.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([O:9][CH2:10][C@H:11]2[CH2:14][CH2:13][NH:12]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 21345251HCID 21345251, compound

Product 1

HCID 21345252HCID 21345252, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-methoxy-3-(1-Cbz-2-(R)-azetidinylmethoxy)pyridine from Example 119c (300 mg, 0.91 mmol) was combined with 10% Pd/C (50 mg) in 30 mL of EtOH, and the mixture was stirred under an H2 atmosphere for 16 hours. The mixture was filtered and concentrated. The crude free base was converted to the salt by treatment with p toluenesulfonic acid in ethyl acetate. The mixture was concentrated, the residue was triturated with ether, and the product was recrystalized from ethyl acetate/ether to give 167 mg (33.9%) of the title compound: mp 139-142° C.; 1H NMR (D2O 300 MHz) δ 2.39 (s, 6H), 2.60-2.70 (m, 2H), 2.98 (s, 3H), 4.04-4.15 (m, 2H), 4.36 (d, J=4.5, 2H), 4.95 (s, 1H), 7.08 (d, J=9.0, 1H), 7.36 (d, J=8.0, 4H), 7.68 (d, J=8.0, 4H), 7.75 (dd, J=3.5, 9.5, 1H), 7.91 (d, J=3.0, 1H); MS (DCI/NH3) m/e 195 (M+H)+. Anal. calcd. for C10H14N2O2.2C7H8O3S: C, 53.52 H, 5.61N, 5.20. Found: C, 53.24 H, 5.68; N, 5.07. [α]D +3.55(c 1, MeOH).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. concentrationThe mixture was concentrated
  4. customthe residue was triturated with ether
  5. customthe product was recrystalized from ethyl acetate/ether

Sources & evidence

ORD record
ord-ffbf9a84c42141ecb53458f950f8f469
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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