4-Bromophenol → 4-(2-(4-Bromophenoxy)ethyl)morpholine

HRID 547411Notes

Reaction equation

S(O)(=O)(=O)C.[O:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18](C3C=CC(CC(NCC4C=CC=CC=4)=O)=NC=3)=[CH:17][CH:16]=2)[CH2:8][CH2:7]1.ClCCN1CCOCC1.[Br:47]C1C=CC(O)=CC=1>>[Br:47][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][N:9]2[CH2:10][CH2:11][O:6][CH2:7][CH2:8]2)=[CH:16][CH:17]=1

Participants

Reactant 3

HCID 78084-Bromophenol

HCID 767274-(2-Chloroethyl)morpholine2×

HCID 25100013Tirbanibulin Mesylate

Product 1

HCID 20538154-(2-(4-Bromophenoxy)ethyl)morpholine

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-b6cbd479d8734749bc008acb77d45443
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939529B2

Reaction notes

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