Acetyl chloride → Hydrochloric Acid

HRID 1397972Notes

Reaction equation

HRID 1397972 reaction equation
C([Cl:4])(=O)C.[CH:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:12][C:13]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:26][CH:27]=3)=[CH:20][N:21]=2)=[O:14])=[CH:9][CH:10]=1>C(O)C>[ClH:4].[ClH:4].[ClH:4].[O:34]1[CH2:33][CH2:32][N:31]([CH2:30][CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([C:19]3[CH:18]=[CH:17][C:16]([CH2:15][C:13]([NH:12][CH2:11][C:8]4[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=4)=[O:14])=[N:21][CH:20]=3)=[CH:23][CH:24]=2)[CH2:36][CH2:35]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 (KX2-391). An HCl solution formed by adding acetyl chloride to absolute ethanol was added to KX2-391 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-62b886465e3d4c90b730ef5143670d85
Source dataset
uspto-grants-2014_12
Patent number
US08901297B2

Reaction notes

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