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

HRID 1032290노트

반응식

HRID 1032290 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f03e1b21a40f4ba9a696e02b3b109258
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04957916

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