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 893686ノート

反応式

HRID 893686 の反応式
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

参加物

7

反応物 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

生成物 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-one収率 67.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2b1649b2eb334d41aa5f273c3994678d
出典データセット
uspto-grants-1992_06
特許番号
US05126339

反応ノート

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