Methanesulfonic Acid → Tirbanibulin Mesylate

HRID 1397973Notes

Reaction equation

HRID 1397973 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][NH:8][C:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:22][CH:23]=3)=[CH:16][N:17]=2)=[O:10])=[CH:5][CH:6]=1.[CH3:33][S:34]([OH:37])(=[O:36])=[O:35]>CC(C)=O>[S:34]([OH:37])(=[O:36])(=[O:35])[CH3:33].[O:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([C:15]3[CH:14]=[CH:13][C:12]([CH2:11][C:9]([NH:8][CH2:7][C:4]4[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=4)=[O:10])=[N:17][CH:16]=3)=[CH:19][CH:20]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 23635314Tirbanibulin

Product 1

HCID 25100013Tirbanibulin Mesylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate (KX2-391•MSA) was synthesized in four linear steps starting from compound 5. The first 3 steps were carried out similar to the procedure discussed above for KX2-391•2HCl to afford methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate (KX2-391). KX2-391 was converted to the methanesulfonate salt by treatment with methanesulfonic acid (MSA) in acetone at 50° C. to afford 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate (KX2-391•MSA).

Sources & evidence

ORD record
ord-cc3c078e6c2c4da18c5218ed8aa92b2e
Source dataset
uspto-grants-2014_12
Patent number
US08901297B2

Reaction notes

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