Hydrochloric Acid → HCID 131734729, compound

HRID 1775118Notes

Reaction equation

HRID 1775118 reaction equation
[CH3:1][C@H:2]1[C@@H:7]([N:8]([C:10]2[N:18]=[CH:17][N:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][NH:14]3)[CH3:9])[CH2:6][N:5]([C:19]([CH2:21][C:22]#[N:23])=[O:20])[CH2:4][CH2:3]1.[ClH:24]>C(O)(C)C>[CH3:1][C@H:2]1[C@@H:7]([N:8]([C:10]2[N:18]=[CH:17][N:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][NH:14]3)[CH3:9])[CH2:6][N:5]([C:19]([CH2:21][C:22]#[N:23])=[O:20])[CH2:4][CH2:3]1.[ClH:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9926791Tofacitinib

Product 1

HCID 131734729HCID 131734729, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
55 °C

Procedure

A suspension of tofacitinib free base (1.0 g, 3.201 mmol) in isopropanol was heated to 55° C. to dissolve. A solution of approximately 17 wt % hydrogen chloride in isopropanol (825 mg, 3.84 mmol) was added. The solution was then cooled to 23 to 25° C. whereupon slightly gummy solids precipitated out. The suspension was stirred at 23 to 25° C. for 64 hours, filtered and washed with isopropanol (2×12 mL). The damp cake was dried under vacuum (45 torr) at 40° C. (24 hours) to yield amorphous tofacitinib hydrochloride (612 mg).

Workup

  1. dissolutionto dissolve
  2. temperatureThe solution was then cooled to 23 to 25° C. whereupon slightly gummy solids
  3. customprecipitated out
  4. filtrationfiltered
  5. washwashed with isopropanol (2×12 mL)
  6. customThe damp cake was dried under vacuum (45 torr) at 40° C. (24 hours)

Sources & evidence

ORD record
ord-836f127203254eceb06806e58232ab70
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Reaction notes

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