Monosodium Citrate → Tofacitinib Citrate

HRID 1775142

Reaction equation

HRID 1775142 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.Br.[C:25]([O-:37])(=[O:36])[CH2:26][C:27]([CH2:32][C:33]([OH:35])=[O:34])([C:29]([OH:31])=[O:30])[OH:28].[Na+]>O>[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.[CH2:32]([C:27]([OH:28])([C:29]([OH:31])=[O:30])[CH2:26][C:25]([OH:37])=[O:36])[C:33]([OH:35])=[O:34]

Participants

4

Reactant 2

HCID 23666341Monosodium CitrateHCID 131734730HCID 131734730, compound

Product 1

HCID 10174505Tofacitinib CitrateYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Amorphous tofacitinib hydrobromide (0.55 g) was dissolved in water (6 mL). The solution was treated with solid monosodium citrate (0.40 g, 1.69 mmol) and the resulting white suspension was stirred for 16 hours at 25° C. The suspension was filtered, washed with water (2×5 mL) and air-dried for 16 hours at 25° C. to yield 0.63 g of tofacitinib citrate as a white solid.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water (2×5 mL)
  3. customair-dried for 16 hours at 25° C.

Sources & evidence

ORD record
ord-749e280bbddb45d38834f9f5890e8c66
Source dataset
uspto-grants-2016_02
Patent number
US09260438B2

Linked notes

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