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

HRID 1699348노트

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HRID 1699348 반응식
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]

참가 물질

5

반응물 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-one2회

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3c1eecfadb5544d0b8999c27a7a5462d
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06346518B1

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