Hydrochloric Acid → HCID 131734729, compound

HRID 1775130Notes

Reaction equation

HRID 1775130 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>CC(C)=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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 9926791Tofacitinib

Product 1

HCID 131734729HCID 131734729, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
24 °C

Procedure

A solution of 4M hydrogen chloride in 1,4-dioxane (3.8 mL, 15.20 mmol) was added to a solution of tofacitinib free base (4.18 g, 13.38 mmol) in acetone (40 mL). The resulting suspension was stirred at 23 to 25° C. for 6 hours, filtered and washed with acetone (2×5 mL) to yield, after air-drying, tofacitinib hydrochloride as a white solid (5.15 g). 1H NMR analysis showed a molar ratio of tofacitinib hydrochloride to acetone of approximately 1:0.88 (12.8 wt %). Water content (KF) was 0.69%.

Workup

  1. filtrationfiltered
  2. washwashed with acetone (2×5 mL)
  3. customto yield
  4. customafter air-drying

Sources & evidence

ORD record
ord-dbdc0e47291d450388ee5d74065daa75
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Reaction notes

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