Hydrochloric Acid → HCID 131734729, compound

HRID 1775124Notes

Reaction equation

HRID 1775124 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>CN(C)C(=O)C>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 9926791Tofacitinib

Product 1

HCID 131734729HCID 131734729, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
24 °C

Procedure

A solution of 4M hydrogen chloride in 1,4-dioxane (2.353 mmol) was added to a suspension of tofacitinib free base (0.7 g, 2.24 mmol) in N,N-dimethylacetamide (10 mL). The clear solution was stirred at 23 to 25° C. (24 hours) and the resulting white suspension was filtered, washed with ethyl acetate (2×5 mL) and air-dried for 16 hours to yield 655 mg of tofacitinib hydrochloride as a white solid. 1H NMR analysis showed a molar ratio of tofacitinib hydrochloride to N,N-dimethylacetamide of approximately 1:0.9 (18.3 wt %). A PXRD taken of this sample is shown in FIG. 8.

Workup

  1. filtrationthe resulting white suspension was filtered
  2. washwashed with ethyl acetate (2×5 mL)
  3. customair-dried for 16 hours

Sources & evidence

ORD record
ord-29065e7459ca49369f4383e1540298c1
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Reaction notes

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