Hydrogen Bromide → Tofacitinib hydrobromide

HRID 1775140Notes

Reaction equation

HRID 1775140 reaction equation
[BrH: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.[BrH:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 9926791Tofacitinib

Product 1

HCID 131734730Tofacitinib hydrobromideYield 100.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

An aqueous solution (48 wt %) of hydrogen bromide (3.44 g, 20.4 mmol) was added to a solution of tofacitinib free base (5.60 g, 17.9 mmol) in acetone (30 mL). The resulting oily suspension was stirred for 1 hour at 25° C. before acetone was removed in vacuo by rotary evaporation and the residual solid was dried under vacuum (8 torr) for 16 hours at 25° C. to yield 7.08 g of amorphous tofacitinib hydrobromide as a pale orange solid. 1H NMR analysis showed a residual acetone content of approximately 1.0 wt %.

Workup

  1. customwas removed in vacuo by rotary evaporation
  2. customthe residual solid was dried under vacuum (8 torr) for 16 hours at 25° C.

Sources & evidence

ORD record
ord-6a8d481a7455486aac01ed74da7fb4bd
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Reaction notes

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