Sodium hydride → Nevirapine

HRID 1510809Notes

Reaction equation

HRID 1510809 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[C:6]([CH3:21])[CH:5]=[CH:4][N:3]=1.[H-].[Na+]>>[CH3:21][C:6]1[CH:5]=[CH:4][N:3]=[C:2]2[N:17]([CH:18]3[CH2:20][CH2:19]3)[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:9](=[O:10])[NH:8][C:7]=12

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 9972204N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide

Product 1

HCID 4463Nevirapine

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-90d4f3b97de947d29991dfbc385bd571
Source dataset
uspto-grants-2012_07
Patent number
US08212025B2

Reaction notes

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