HCID 14854959、化合物 → HCID 178493191、化合物

HRID 1165050ノート

反応式

HRID 1165050 の反応式
CS[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=1.[NH2:10][C:11]1[C:31]([Cl:32])=[CH:30][C:14]([C:15]([NH:17][C@H:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][NH2:27])[CH2:20][C@H:19]2[O:28][CH3:29])=[O:16])=[C:13]([O:33][CH3:34])[CH:12]=1>C(#N)C>[OH2:9].[NH2:10][C:11]1[C:31]([Cl:32])=[CH:30][C:14]([C:15]([NH:17][C@H:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][NH:27][C:3]3[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=3)[CH2:20][C@H:19]2[O:28][CH3:29])=[O:16])=[C:13]([O:33][CH3:34])[CH:12]=1

参加物

4

反応物 2

HCID 14854959HCID 14854959、化合物HCID 178503462HCID 178503462、化合物2 回

生成物 1

HCID 178493191HCID 178493191、化合物収率 39.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 1.56 parts of 2-(methylthio)-4-pyrimidinol, 3.7 parts of cis-4-amino-N-[1-(3-aminopropyl)-3-methoxy-4-piperidinyl]-5-chloro-2-methoxybenzamide and 64 parts of acetonitrile was stirred for 40 hours at reflux temperature. Another portion of 0.7 parts of 2-(methylthio)-4-pyrimidinol was added and stirring was continued over weekend at reflux temperature. The reaction mixture was evaporated. The residue was taken up in trichloromethane. The whole was washed with water, saturated with ammonium hydroxide, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5by 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 1.82 parts (39.5%) of cis-4-amino-5-chloro-N-[1-[3-[(4-hydroxy-2-pyrimidinyl)amino]propyl]-3-methoxy-4-piperidinyl]- 2-methoxybenzamide monohydrate; mp. 134.2° C. (compound 42).

後処理

  1. temperatureat reflux temperature
  2. stirringstirring
  3. waitwas continued over weekend
  4. temperatureat reflux temperature
  5. customThe reaction mixture was evaporated
  6. washThe whole was washed with water, saturated with ammonium hydroxide
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe residue was crystallized from acetonitrile
  15. filtrationThe product was filtered off
  16. customdried

出典と根拠

ORDレコード
ord-f39b36014c7546d6ada50e5760a91e3e
出典データセット
uspto-grants-1990_03
特許番号
US04906643

反応ノート

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