Acetonitrile → 2-(5-(4-(2-Morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile
Reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:23](#[N:25])[CH3:24]>>[O:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][O:12][C:11]2[CH:21]=[CH:22][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH2:24][C:23]#[N:25])=[N:7][CH:6]=3)=[CH:9][CH:10]=2)[CH2:16][CH2:17]1Participants
Procedure
In another aspect, the invention relates to a process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride 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 hydrochloric acid to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride.
Sources & evidence
- ORD record
- ord-c9e1275f1f0047a2864c8429ad42902f
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309549B2
Reaction notes
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