Potassium Iodide → 2-methyl-3-[2-[4-[[1-(2-pyrazinylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1493929노트

반응식

HRID 1493929 반응식
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]2=[N:6][C:5]=1[CH3:15].Br.Br.Br.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]2[N:30]([CH2:31][C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)[C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]=3[N:27]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CN(C)C(=O)C>[CH3:15][C:5]1[N:6]=[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][N:8]2[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][N:19]1[CH2:20][CH2:21][CH:22]([NH:25][C:26]2[N:30]([CH2:31][C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)[C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]=3[N:27]=2)[CH2:23][CH2:24]1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 8178663-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 19890729N-(4-piperidinyl)-1-(2-pyrazinylmethyl)-1H-benzimidazol-2-amine trihydrobromide

생성물 1

HCID 139832072-methyl-3-[2-[4-[[1-(2-pyrazinylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one수율 67.4%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

A mixture of 3.15 parts of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 8.26 parts of N-(4-piperidinyl)-1-(2-pyrazinylmethyl)-1H-benzimidazol-2-amine trihydrobromide, 6.4 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylacetamide was stirred and heated overnight at 80° C. The reaction mixture was poured into water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 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 5 parts (67.4%) of 2-methyl-3-[2-[4-[[1-(2-pyrazinyl-methyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4H-pyrido-[1,2-a]pyrimidin-4-one; mp. 204.4° C. (compound 68).

후처리

  1. extractionThe product was extracted with trichloromethane
  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
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from acetonitrile
  10. filtrationThe product was filtered off
  11. customdried

출처 및 근거

ORD 기록
ord-c43c7641a13d49aeaa2868b22282177c
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05025014

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