Sodium ethanethiolate → 3-Chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-1-methyl-1-H-1,2,4-triazol-3-yl}phenol

HRID 22844

反応式

HRID 22844 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[C:10]1[N:14](C)[N:13]=[C:12]([C:16]23[CH2:23][CH2:22][C:19]([CH2:24][CH2:25][CH2:26][CH:27]([OH:29])[CH3:28])([CH2:20][CH2:21]2)[CH2:18][CH2:17]3)[N:11]=1.[CH2:30]([S-])C.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([C:16]23[CH2:23][CH2:22][C:19]([CH2:24][CH2:25][CH2:26][CH:27]([OH:29])[CH3:28])([CH2:18][CH2:17]2)[CH2:20][CH2:21]3)[N:13]([CH3:30])[N:14]=1

参加物

4

反応物 2

HCID 4459711Sodium ethanethiolate2 回HCID 865933835-{4-[5-(2-Chloro-4-methoxyphenyl)-1-methyl-1-H-1,2,4-triazol-3-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-ol

生成物 1

HCID 1358707353-Chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-1-methyl-1-H-1,2,4-triazol-3-yl}phenol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

5-{4-[5-(2-Chloro-4-methoxyphenyl)-1-methyl-1-H-1,2,4-triazol-3-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-ol (5-J) (0.036 g, 0.086 mmol) was placed in a small vial with 0.5 mL of DMF. Sodium ethanethiolate (0.0218 g, 0.260 mmol) was added to the solution. The vial was sealed and heated to 100° C. for 1.5 h. The incomplete reaction required another 1.5 equivalents of sodium ethanethiolate (0.011 g). The vial was resealed and heated at 100° C. for 1 h. The product, 3-chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-1-methyl-1-H-1,2,4-triazol-3-yl}phenol (5-K) was purified by preparative reverse phase HPLC on a C-18 silica gel column using a gradient of acetonitrile-water buffered with 0.1% trifluoroacetic acid. The effluent containing the pure triazole was made basic with 10% NaHCO3, evaporated in vacuo to remove most of the acetonitrile, and extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated, and the residue dried under vacuum to provide the desired compound. MS (ESI+)=404.4 (M+1).

後処理

  1. customThe vial was sealed
  2. customThe incomplete reaction
  3. temperatureheated at 100° C. for 1 h
  4. customThe product, 3-chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-1-methyl-1-H-1,2,4-triazol-3-yl}phenol (5-K) was purified by preparative reverse phase HPLC on a C-18 silica gel column
  5. additionThe effluent containing the pure triazole
  6. customevaporated in vacuo
  7. customto remove most of the acetonitrile
  8. extractionextracted with methylene chloride
  9. extractionThe organic extract
  10. dry with materialwas dried (MgSO4)
  11. customevaporated
  12. customthe residue dried under vacuum

出典と根拠

ORDレコード
ord-bde1fed8a4d247b3a07bde2dba0a6c7e
出典データセット
uspto-grants-2005_02
特許番号
US06849636B2

関連ノート

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