Preparation of N1-(2′-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines
AssigneeWyeth
InventorsAnita Wai-Yin Chan, Gregg Brian Feigelson, Joseph Zeldis, Ivo Jirkovsky
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Abstract
A process for making an N1-(2′-pyridyl)-1,2-alkanediamine sulfamic acid of formula II by reacting a compound of formula I with NH2R′ wherein R and R′ are as defined in the specification. The invention also includes the compound of formula II, and optical isomers thereof. The compound of formula II is an intermediate useful for making chiral piperazine derivatives which are active at the 5-HT1A receptor.
Claims15
A process for making an N1-(2′-pyridyl)-1,2-alkanediamine sulfamic acid of formula II comprising reacting a compound of formula I with NH2R′
- wherein R is selected from the group consisting of C1-C3 alkyl, and R′ is H, C1-C6 alkyl, C3-C7 cycloalkyl, C2-C7 acyl, C5-C10 aryl C6-C11 aroyl, (C3-C7)cycloalkyl(C1-C6)alkyl, di-(C3-C7)cycloalkyl-(C1—C6)alkyl, (C5-C10)aryl(C1-C6)alkyl, and di-(C5-C10)aryl-(C1-C6)alkyl.
A process for converting a compound of formula II
- wherein R is selected from the group consisting of C1-C3 alkyl, and R′ is H, C1-C6 alkyl, C3-C7 cycloalkyl, C2-C7 acyl, C5-C10 aryl C6-C11 aroyl, (C3-C7)cycloalkyl(C1-C6)alkyl, di-(C3-C7)cycloalkyl-(C1—C6)alkyl, (C5-C10)aryl(C1-C6)alkyl, and di-(C5-C10)aryl-(C1-C6)alkyl, to a compound of formula III
- said process comprising the steps of:
- a) where R′ is not H, hydrogenating the compound of formula II to convert R′ to H;
- and,
- b) acid hydrolysis of the compound of formula II in which R′ is H, to form a compound of formula III.
A process comprising reacting the compound of formula II with a compound of formula IV to form a compound of formula V
- wherein Ar is a dihydrobenzodioxinyl or benzodioxinyl, or phenyl optionally substituted with up to three substituents independently selected from halogen, methoxy, halomethyl, dihalomethyl and trihalomethyl, and L is a suitable leaving group.
A compound of formula II
- wherein R is selected from the group consisting of C1-C3 alkyl, and R′ is selected from the group consisting of H, C1-C6 alkyl, C3-C7 cycloalkyl, C2-C7 acyl, C5-C10 aryl C6-C11 aroyl, (C3-C7)cycloalkyl(C1-C6)alkyl, di-(C3-C7)cycloalkyl -(C1-C6)alkyl, (C5-C10)aryl(C1-C6)alkyl, and di-(C5-C10)aryl-(C1-C6)alkyl, and optical isomers thereof.
Dependencies are inferred from the claim text.