Sodium Hydroxide → Tofacitinib

HRID 44416Notes

Reaction equation

HRID 44416 reaction equation
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH3:14][C@@H:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:25])[CH2:22][C:23]#[N:24])[CH2:17][C@@H:16]1[N:26]([CH3:36])[C:27]1[C:28]2[CH:35]=[CH:34][NH:33][C:29]=2[N:30]=[CH:31][N:32]=1.[OH-].[Na+]>ClCCl>[CH3:14][C@@H:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:25])[CH2:22][C:23]#[N:24])[CH2:17][C@@H:16]1[N:26]([CH3:36])[C:27]1[C:28]2[CH:35]=[CH:34][NH:33][C:29]=2[N:30]=[CH:31][N:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10174505Tofacitinib Citrate

Product 1

HCID 9926791Tofacitinib

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile citrate salt, as prepared in Method F above, was treated with 1M sodium hydroxide in dichloromethane to afford the corresponding free base. The free base was then crystallized from methanol and water to furnish the crystal form of the free base.

Workup

  1. customto afford the corresponding free base
  2. customThe free base was then crystallized from methanol and water
  3. customto furnish the crystal form of the free base

Sources & evidence

ORD record
ord-dd5e687f68734ce78f2de041aa7cd23a
Source dataset
uspto-grants-2013_09
Patent number
US08541426B2

Reaction notes

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