1,4-Dioxane → 6-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3-pyridinecarboxamide fumarate

HRID 534801노트

반응식

HRID 534801 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:32])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:31])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].O1CCOCC1>CC(CC(C)C)=O>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:32])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:31])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 444972Fumaric AcidHCID 237290236-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3-pyridinecarboxamide

생성물 1

HCID 675263896-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3-pyridinecarboxamide fumarate

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매2회

실험 절차

A solution of E2 free base (57.5 mg) in methyl iso-butylketone (0.5 mL) was added to fumaric acid (13.4 mg). Further methyl iso-butylketone (0.5 mL) was added and the mixture was heated with a hot air gun. The resulting yellow gum was scratched with a spatula and a small amount of white solid appeared throughout the gum. The sample was placed on a shaker block and temperature cycled (0-40° C. in 1 h blocks) over the weekend. To the resulting yellow gum in a colourless solution was added 1,4-dioxane (0.5 mL) and the mixture was heated to dissolve the gum. On cooling a gum formed and the sample was temperature cycled as before. After a period of ˜6 weeks a white solid slurry had formed. The mixture was placed back in the shaker block and temperature cycled as before, overnight. The mixture was then left to equilibrate to room temperature and the white solid was collected by filtration. After drying at 40° C. under vacuum overnight the title compound was obtained as a white, mainly crystalline powder (38.7 mg). M.pt. onset ˜150° C.

후처리

  1. temperaturethe mixture was heated with a hot air gun
  2. custom(0-40° C. in 1 h blocks)
  3. temperaturethe mixture was heated
  4. dissolutionto dissolve the gum
  5. temperatureOn cooling a gum
  6. customformed
  7. customAfter a period of ˜6 weeks a white solid slurry had formed
  8. customovernight
  9. waitThe mixture was then left
  10. customto equilibrate to room temperature
  11. filtrationthe white solid was collected by filtration
  12. dry with materialAfter drying at 40° C. under vacuum overnight the title compound

출처 및 근거

ORD 기록
ord-bd4bcc842bb94a249ddfee9ebd0638fd
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853218B2

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