3-Amino-2-chloro-4-methylpyridine → 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

HRID 1510808Notes

Reaction equation

HRID 1510808 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>>[Cl:10][C:11]1[C:12]([C:13]([NH:1][C:2]2[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=2[CH3:8])=[O:14])=[CH:16][CH:17]=[CH:18][N:19]=1

Participants

3

Reactant 2

HCID 27563873-Amino-2-chloro-4-methylpyridineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 104238682-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

Procedure

3-Amino-2-chloro-4-methylpyridine of Formula A is condensed with 2-chloronicotinoyl chloride of Formula B to give 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide of Formula II, which is then reacted with cyclopropylamine to give N-(2-chloro-4-methyl-3-pyridyl)-2 -cyclopropylamino) -3-pyridine carboxamide of Formula III. Then N-(2-chloro-4-methyl-3-pyridyl)-2-(cyclopropylamino)-3-pyridine carboxamide was cyclized in the presence of sodium hydride to give nevirapine of Formula I. The disadvantage of the above process is use of large excess of cyclopropylamine. Further, with the above process undesirable side products are obtained during the reaction, which makes the product impure.

Sources & evidence

ORD record
ord-354312b1924a4698a218edc3c036dff7
Source dataset
uspto-grants-2012_07
Patent number
US08212025B2

Reaction notes

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