Hydrochloric Acid → HCID 131734729, compound

HRID 1775131Notes

Reaction equation

HRID 1775131 reaction equation
[ClH:1].O1CCOCC1.[CH3:8][C@H:9]1[C@@H:14]([N:15]([C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[CH:19]=[CH:20][NH:21]3)[CH3:16])[CH2:13][N:12]([C:26]([CH2:28][C:29]#[N:30])=[O:27])[CH2:11][CH2:10]1.C(OCC)(=O)C>[N+](C)([O-])=O>[CH3:8][C@H:9]1[C@@H:14]([N:15]([C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[CH:19]=[CH:20][NH:21]3)[CH3:16])[CH2:13][N:12]([C:26]([CH2:28][C:29]#[N:30])=[O:27])[CH2:11][CH2:10]1.[ClH:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 9926791Tofacitinib

Product 1

HCID 131734729HCID 131734729, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A solution of 4M hydrogen chloride in 1,4-dioxane (0.6 mL, 2.353 mmol) was added to a solution of tofacitinib free base (0.7 g, 2.24 mmol) in nitromethane (6 mL). Gummy solids were obtained when ethyl acetate (6 mL) was added. Stirring was continued at 23 to 25° C. for 23 hours and the resulting white suspension was filtered, washed with ethyl acetate (2×5 mL) and air-dried to yield 800 mg of tofacitinib hydrochloride as a white solid. 1H NMR analysis showed a molar ratio of tofacitinib hydrochloride to nitromethane of approximately 1:0.009 (0.1 wt %). A PXRD taken of this sample is shown in FIG. 11.

Workup

  1. additionwas added
  2. filtrationthe resulting white suspension was filtered
  3. washwashed with ethyl acetate (2×5 mL)
  4. customair-dried

Sources & evidence

ORD record
ord-1e3f660d9f19437fa4ce6b2180a82c1a
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Reaction notes

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