Dimethylformamide → 2-(1-Methylpropyl)-3H-1,2,4-triazole-3-one

HRID 1699348Notes

Reaction equation

OC1C=CC(N2CCN(C3C=CC([N:20]4[CH:24]=[N:23][N:22]([C@@H:25]([CH3:28])[CH2:26][CH3:27])[C:21]4=[O:29])=CC=3)CC2)=CC=1.[OH-].[Na+].CN(C)C=O>O>[CH3:28][CH:25]([N:22]1[C:21](=[O:29])[NH:20][CH:24]=[N:23]1)[CH2:26][CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6.7 g of (+)-(2R,cis)-2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolane-4-methanol 4-methylbenzenesulfonate(ester) 4-methyl-benzenesulfonate(salt 1:1) (intermediate (10)), 3.9 g of (+)-(S)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one (intermediate (7)), 1.5 g of sodium hydroxide flakes and 100 ml of N,N-dimethylformamide was stirred overnight at 50° C. under a nitrogen atmosphere. After cooling, water was added to the reaction mixture. The precipitate was filtered off and taken up in dichloromethane. The organic layer was dried, filtered and evaporated. The residue was triturated with methanol, yielding 5.6 g (83.2%) of (+)-[2R-[2α,4α,4(S)]]-4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one; mp. 182.4° C.; [α]D20=+14.130° (c=1% in methanol) (comp. 8).

Workup

temperatureAfter cooling
filtrationThe precipitate was filtered off
customThe organic layer was dried
filtrationfiltered
customevaporated
customThe residue was triturated with methanol

Sources & evidence

ORD record: ord-3c1eecfadb5544d0b8999c27a7a5462d
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346518B1

Reaction notes

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