Benzylamine → Tirbanibulin

HRID 547414Notes

Reaction equation

HRID 547414 reaction equation
B(O)(O)C1C=CC(F)=NC=1.O1CCN(CCOC2C=CC(C3C=CC(CC#N)=NC=3)=CC=2)CC1.[O:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][O:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:51]=[CH:52][C:53]([CH2:56][C:57](OC)=[O:58])=[N:54][CH:55]=3)=[CH:46][CH:45]=2)[CH2:37][CH2:36]1.FC1N=CC(C2C=CC(OCCN3CCOCC3)=CC=2)=CC=1.[CH2:83]([NH2:90])[C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1>>[O:35]1[CH2:36][CH2:37][N:38]([CH2:41][CH2:42][O:43][C:44]2[CH:45]=[CH:46][C:47]([C:50]3[CH:51]=[CH:52][C:53]([CH2:56][C:57]([NH:90][CH2:83][C:84]4[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=4)=[O:58])=[N:54][CH:55]=3)=[CH:48][CH:49]=2)[CH2:39][CH2:40]1

Participants

6

Reactant 5

HCID 7504BenzylamineHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 441854204-(2-(4-(6-Fluoropyridin-3-yl)phenoxy)ethyl)morpholineHCID 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 a process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate comprising the steps of: (1) reacting 4-(2-chloroethyl)morpholine with 4-bromophenol to yield 4-(2-(4-bromophenoxy)ethyl)morpholine; (2) coupling 4-(2-(4-bromophenoxy)ethyl)morpholine with 6-fluoropyridin-3-yl-3-boronic acid to yield 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine; (3) 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; (4) converting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile to methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate; (5) 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; and (6) contacting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide with methane sulfonic acid to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate.

Sources & evidence

ORD record
ord-9052208f6ca84997ab9a967fc97fb55d
Source dataset
uspto-grants-2011_05
Patent number
US07939529B2

Reaction notes

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