p-Toluenesulfonic acid monohydrate → HCID 21345177, compound

HRID 367088Notes

Reaction equation

HRID 367088 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2C(OCC2C=CC=CC=2)=O)=[CH:6][CH:5]=[C:4]([CH3:24])[N:3]=1.O.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>CCO.[Pd]>[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)([OH:35])(=[O:34])=[O:33].[F:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=[C:4]([CH3:24])[N:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21345174HCID 21345174, compound

Product 1

HCID 21345177HCID 21345177, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-6-methyl-3-(1-Cbz-2-(S)-azetidinylmethoxy)pyridine from Example 117d (714 mg, 2.16 mmol) was combined with 10% Pd/C (50 mg) and p-toluenesulfonic acid monohydrate (830 mg, 4.36 mmole) in 30 mL of EtOH, and the mixture was stirred under an H2 atmosphere for 16 hours. The mixture was filtered, concentrated, the residue was triturated with ether, and the product was recrystallized from ethyl acetate/ether to yield 480 mg (60%) of the title compound. mp 141-143° C. 1H NMR (D2O 300 MHz) δ: 2.40 (s, 6H), 2.65-2.71 (m, 2H), 4.07-4.16 (m, 2H), 4.43(d, J=4.5, 2H), 4.81-95 (m, 1H), 7.16 (d, J=8.0, 1H), 7.37 (d,J=8.0, 2H), 7.55 (dd, J=8.0, 2.5, 1H), 7.70 (d,J=8.0, 2H). MS (DCI/NH3) m/e 197 (M+H)+ 214 (M+NH4)+. Anal. calcd. for C10H13FN2O.C7H8O3S: C, 55.42 H, 5.75 N, 7.60. Found: C, 55.27 H, 5.69; N, 7.44. [α]D -3.2 (c 1, MeOH).

Workup

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

Sources & evidence

ORD record
ord-61ff75ba8b3f44f78eaf05e3b5b2a05f
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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