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

HRID 1699348ノート

反応式

HRID 1699348 の反応式
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]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 9918902,4-Dihydro-4-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)-2-((1S)-1-methylpropyl)-3H-1,2,4-triazol-3-one2 回

生成物 1

HCID 1357235282-(1-Methylpropyl)-3H-1,2,4-triazole-3-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered off
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with methanol

出典と根拠

ORDレコード
ord-3c1eecfadb5544d0b8999c27a7a5462d
出典データセット
uspto-grants-2002_02
特許番号
US06346518B1

反応ノート

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