Methanesulfonate → Safinamide Mesylate

HRID 41737Notes

Reaction equation

FC1C=C(C=CC=1)COC1C=CC(C=O)=CC=1.[F:18][C:19]1[CH:20]=[C:21]([CH:37]=[CH:38][CH:39]=1)[CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:27]([CH2:28][NH:29][C@@H:30]([CH3:34])[C:31]([NH2:33])=[O:32])=[CH:26][CH:25]=1.[CH3:40][S:41]([O-:44])(=[O:43])=[O:42]>>[CH3:40][S:41]([OH:44])(=[O:43])=[O:42].[F:18][C:19]1[CH:20]=[C:21]([CH:37]=[CH:38][CH:39]=1)[CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][NH:29][C@@H:30]([CH3:34])[C:31]([NH2:33])=[O:32])=[CH:35][CH:36]=1

Participants

Reactant 3

HCID 85257Methanesulfonate

HCID 131682Safinamide

HCID 8801194-[(3-Fluorophenyl)methoxy]benzaldehyde

Product 1

HCID 3038502Safinamide MesylateYield 87%

Procedure

The product of the title is prepared in a 87% yield by following the same procedure of Example 12 a1) with the exception that the 4-(3-fluorobenzyloxy)benzaldehyde is prepared according to Example 11 and converted the thus obtained (S)-2-[4-(3-fluorobenzyloxy)benzylamino]propanamide into the methanesulfonate (Ic), having 99.7 (area %) purity, determined according to the method of Example 25A and the content of the C,O-dialkylated impurity (IIa) is 0.005% by weight, measured by the method of Example 25B.

Workup

customThe product of the title is prepared in a 87% yield
customis prepared

Sources & evidence

ORD record: ord-abae2211a3a04e02b195383b7b927478
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530701B2

Reaction notes

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