Sodium Carbonate → 6-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one

HRID 484736

반응식

HRID 484736 반응식
Br.Br[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[C:12]([CH3:15])=[CH:13][S:14][C:8]2=[N:7][C:6]=1[CH3:16].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.CC(C)CC(=O)C>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C:24]([C:21]2[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=2)=[C:25]2[CH2:30][CH2:29][N:28]([CH2:3][CH2:4][C:5]3[C:10](=[O:11])[N:9]4[C:12]([CH3:15])=[CH:13][S:14][C:8]4=[N:7][C:6]=3[CH3:16])[CH2:27][CH2:26]2)=[CH:32][CH:33]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 10942334Sodium MethoxideHCID 139830776-(2-Bromoethyl)-3,7-dimethyl-5H-thiazolo[3,2-A]pyrimidin-5-one monohydrobromide

생성물 1

HCID 133631946-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one수율 72.8%

시약·촉매·용매 2

HCID 962Water용매HCID 7909Methyl Isobutyl Ketone용매

실험 절차

A mixture of 5.6 parts of 6-(2-bromoethyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide, 3.5 parts of 4-[bis(4-fluorophenyl)methylene]piperidine, 1 part of a sodium methoxide solution 30%, 8 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours using a water-separator. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 4.3 parts (72.8%) of 6-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 183.8° C. (compound 112).

후처리

  1. temperaturerefluxed for 20 hours
  2. filtrationThe reaction mixture was filtered while hot and the filtrate
  3. customwas evaporated
  4. customThe residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-3c1761841dc94f6a9c07fffd9f7451c0
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04533665

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