Acetyl chloride → Hydrochloric Acid

HRID 403218Notes

Reaction equation

HRID 403218 reaction equation
C([Cl:4])(=O)C.[O:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])=[N:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:7][CH2:6]1>C(O)C>[ClH:4].[ClH:4].[ClH:4].[O:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])=[N:24][CH:25]=3)=[CH:18][CH:19]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 23635314Tirbanibulin

Product 2

HCID 313Hydrochloric AcidHCID 24989633N-Benzyl-2-(5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}pyridin-2-yl)acetamide--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The resulting methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate (7) and benzyl amine were coupled in anisole at high temperature to afford 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide (Compound 134). An HCl solution formed by adding acetyl chloride to absolute ethanol was added to Compound 134 to form the bis-HCl salt, 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride, (KX2-di-HCl).

Sources & evidence

ORD record
ord-ab257d0b77fc441db0bbd9164082b43d
Source dataset
uspto-grants-2014_06
Patent number
US08748423B2

Reaction notes

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