Sodium Carbonate → 3-Bromo-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine

HRID 484512노트

반응식

HRID 484512 반응식
[Br:1][C:2]1[N:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.[O:9]1[CH2:13][CH2:12][N:11]=[C:10]1[C:14]1[CH:29]=[CH:28][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:1][C:2]1[N:3]=[N:4][C:5]([N:25]2[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:18][C:17]3[CH:16]=[CH:15][C:14]([C:10]4[O:9][CH2:13][CH2:12][N:11]=4)=[CH:29][CH:28]=3)[CH2:23][CH2:24]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 2488523,6-DibromopyridazineHCID 149891791-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]piperazine

생성물 1

HCID 149892973-Bromo-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine수율 16.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

A mixture of 4.1 parts of 3,6-dibromopyridazine, 4.34 parts of 1-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]piperazine, 6.4 parts of sodium carbonate and 1878 parts of N,N-dimethylformamide was stirred overnight at 65° C. The reaction mixture was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol 98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 1.1 parts (16.4%) of 3-bromo-6-[4-[3-[4(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine; mp. 169.1° C. (comp. 75).

후처리

  1. extractionthe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol 98.5:1.5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 2-propanol
  10. filtrationThe product was filtered off
  11. customdried

출처 및 근거

ORD 기록
ord-88af42f5eb6e40948beb22d5d10e5c98
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05231184

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