Benzylamine → Tirbanibulin

HRID 1397987Notes

Reaction equation

HRID 1397987 reaction equation
O1CCN(CCOC2C=CC(C3C=CC(CC#N)=NC=3)=CC=2)CC1.[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:41]=[CH:42][C:43]([CH2:46][C:47](OC)=[O:48])=[N:44][CH:45]=3)=[CH:36][CH:35]=2)[CH2:27][CH2:26]1.[CH2:51]([NH2:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>>[O:25]1[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][O:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]3[CH:41]=[CH:42][C:43]([CH2:46][C:47]([NH:58][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[O:48])=[N:44][CH:45]=3)=[CH:38][CH:39]=2)[CH2:29][CH2:30]1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 441854212-(5-(4-(2-Morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrileHCID 44185422Methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate2×

Product 1

HCID 23635314Tirbanibulin

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-aa8f0446ba794f9ebaa3c8bbfd921a72
Source dataset
uspto-grants-2014_12
Patent number
US08901297B2

Reaction notes

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