Sodium Carbonate → cis-4-amino-5-chloro-5-methoxy-N-[3-methoxy-1-[3-(2-pyrimidinylamino)propyl]-4-piperidinyl]benzamide

HRID 654180ノート

反応式

HRID 654180 の反応式
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[C:29]([Cl:30])=[CH:28][C:12]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][NH2:25])[CH2:18][C@H:17]2[O:26][CH3:27])=[O:14])=[C:11](OC)[CH:10]=1.[C:33](=O)([O-])[O-:34].[Na+].[Na+]>CN(C)C(=O)C>[NH2:8][CH:9]1[C:29]([Cl:30])([O:34][CH3:33])[CH:28]=[C:12]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][NH:25][C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:18][C@H:17]2[O:26][CH3:27])=[O:14])[CH:11]=[CH:10]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 14854959HCID 14854959、化合物

生成物 1

HCID 67915924cis-4-amino-5-chloro-5-methoxy-N-[3-methoxy-1-[3-(2-pyrimidinylamino)propyl]-4-piperidinyl]benzamide収率 35%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1.17 parts of 2-chloropyrimidine, 5.56 parts of cis-4-amino-N-[1-(3-aminopropyl)-3-methoxy-4-piperidinyl]-5-chloro-2-methoxybenzamide and 2.7 parts of N,N-dimethylacetamide was stirred for 6.5 hours at 90° C. After cooling, a sodium carbonate solution was added. 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, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.4 parts (35%) of cis-4-amino-5-chloro-5-methoxy-N-[3-methoxy-1-[3-(2-pyrimidinylamino)propyl]-4-piperidinyl]benzamide; mp. 158.5° C. (compound 36).

後処理

  1. temperatureAfter cooling
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

出典と根拠

ORDレコード
ord-f2e804d24cbd41608327a60fe1689784
出典データセット
uspto-grants-1992_07
特許番号
US05130312

反応ノート

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