Tirbanibulin → 2-(5-(4-(2-Morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile

HRID 1397986Notes

Reaction equation

HRID 1397986 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]([NH:25]CC4C=CC=CC=4)=O)=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.FC1N=CC(C2C=CC(OCCN3CCOCC3)=CC=2)=CC=1>C(#N)C>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]#[N:25])=[N:20][CH:21]=3)=[CH:14][CH:15]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 23635314TirbanibulinHCID 441854204-(2-(4-(6-Fluoropyridin-3-yl)phenoxy)ethyl)morpholine

Product 1

HCID 441854212-(5-(4-(2-Morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In another aspect, the invention relates to the process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide comprising the steps of reacting 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine with acetonitrile to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile; converting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile to methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate; and reacting methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate with benzylamine to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide.

Sources & evidence

ORD record
ord-8f77f9c07f8f4da58e6ef8353bc1fcbe
Source dataset
uspto-grants-2014_12
Patent number
US08901297B2

Reaction notes

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