Hydrochloric Acid → HCID 131734729, compound

HRID 1775132Notes

Reaction equation

HRID 1775132 reaction equation
[ClH:1].[CH3:2][C@H:3]1[C@@H:8]([N:9]([C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH3:10])[CH2:7][N:6]([C:20]([CH2:22][C:23]#[N:24])=[O:21])[CH2:5][CH2:4]1>CC(C)=O>[CH3:2][C@H:3]1[C@@H:8]([N:9]([C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH3:10])[CH2:7][N:6]([C:20]([CH2:22][C:23]#[N:24])=[O:21])[CH2:5][CH2:4]1.[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9926791Tofacitinib

Product 1

HCID 131734729HCID 131734729, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 37% aqueous hydrogen chloride (240 mg, 2.36 mmol) was added to a solution of tofacitinib free base (0.7 g, 2.24 mmol) in acetone (10 mL). Stirring was continued at 23 to 25° C. for 23 hours and the resulting white suspension was filtered, washed with acetone (2×5 mL) and air-dried to yield 820 mg of tofacitinib hydrochloride as a white solid. 1H NMR analysis showed a molar ratio of tofacitinib hydrochloride to acetone of approximately 1:0.13 (2.1 wt %). A PXRD taken of this sample is shown in FIG. 12.

Workup

  1. filtrationthe resulting white suspension was filtered
  2. washwashed with acetone (2×5 mL)
  3. customair-dried

Sources & evidence

ORD record
ord-34ec74ad7a994adc8725ebf1e4e2e849
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Reaction notes

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