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 2309520노트

반응식

HRID 2309520 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

반응 조건

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-pyrazinylmethyl)-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-8c665c536f2240b382921d4bb614bfee
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695569

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