p-Toluenesulfonic acid monohydrate → HCID 21345177, compound

HRID 2185754Notes

Reaction equation

HRID 2185754 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.C7H8S: 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-fe6d88397cc54135af1c0ceec71193ca
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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