1-Butanol → 6-fluoro-3-[4-(phenylmethyl)piperazinyl]-1H-indazole

HRID 2051012ノート

反応式

HRID 2051012 の反応式
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=S)[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.C(O)CCC.O.[NH2:30][NH2:31].C(=O)([O-])[O-].[Na+].[Na+]>CC1C=CC=CC=1.O.C(O)(=O)C>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)=[N:30][NH:31]2)=[CH:4][CH:5]=1

参加物

8

反応物 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 150574521-[(2,4-Difluorophenyl)thioxomethyl]-4-(phenylmethyl)piperazine

生成物 1

HCID 150574536-fluoro-3-[4-(phenylmethyl)piperazinyl]-1H-indazole収率 32.2%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A mixture of 40 parts of 1-[(2,4-difluorophenyl)thioxomethyl]-4-(phenylmethyl)piperazine, 144 parts of 1-butanol, 13 parts of hydrazine monohydrate and 24 parts of acetic acid was stirred overnight at reflux temperature. After cooling, 50 parts of sodium carbonate were added and stirring was continued for 3 hours at reflux temperature. The reaction mixture was cooled until room temperature and water and methylbenzene were added. After stirring for 15 minutes, the separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 12 parts (32.2%) of 6-fluoro-3-[4-(phenylmethyl)piperazinyl]-1H-indazole; mp. 162.0° C. (int. 7).

後処理

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. stirringstirring
  4. waitwas continued for 3 hours
  5. temperatureat reflux temperature
  6. stirringAfter stirring for 15 minutes
  7. customthe separated organic layer was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe residue was crystallized from acetonitrile
  15. filtrationThe product was filtered off
  16. customdried

出典と根拠

ORDレコード
ord-95eb9948ff8a415aa5251bd8bd9370e5
出典データセット
uspto-grants-1991_05
特許番号
US05015740

反応ノート

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