2-Bromo-4,6-dimethylpyridine → (+/-)-2-[1-(4-chlorobenzoyl)propyl]-4-[6-[4-(4,6-dimethyl-2-pyridinyl)-1-piperazinyl]-3-pyridinyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 974816Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([CH:8]([N:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:21][CH:22]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[N:33]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([CH:8]([N:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:24][CH2:25][N:26]([C:32]5[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[N:33]=5)[CH2:27][CH2:28]4)=[CH:21][CH:22]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

(±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-(1-piperazinyl)-3-pyridinyl]-3H-1,2,4-triazol-3-one (6.02 g) and 2-bromo-4,6-dimethylpyridine (5.25 g) were stirred and heated under N2 at 140° C. for 2 days. The mixture was dissolved in CH2Cl2 and purified on a glass filter over silica gel (eluent: CH2Cl2 /CH3OH 100/0 to 97/3). The pure fractions were collected and evaporated, yielding 3.6 g (48%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-4-[6-[4-(4,6-dimethyl-2-pyridinyl)-1-piperazinyl]-3-pyridinyl]-2,4-dihydro-3H-1,2,4-triazol-3-one; mp. 113.2° C. (comp. 32).

Workup

custompurified on a glass
filtrationfilter over silica gel (eluent: CH2Cl2 /CH3OH 100/0 to 97/3)
customThe pure fractions were collected
customevaporated

Sources & evidence

ORD record: ord-d089eb0b1ec3449a9de4d8c903de00a0
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05607932

Reaction notes

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