2-Aminopyridine → N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-(imidazo[1,2-a]-pyridin-2-yl)benzamide

HRID 2384368ノート

反応式

HRID 2384368 の反応式
C([O:8][C:9]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33]Br)=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)=[O:12])C1C=CC=CC=1.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:25][C:24]([F:26])([F:27])[C:16]1[CH:15]=[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:28]=[C:29]([C:32]3[N:36]=[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]4[CH:33]=3)[CH:30]=[CH:31][C:9]=2[OH:8])[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=1

参加物

5

反応物 3

HCID 104392-AminopyridineHCID 516892Sodium Bicarbonate2 回HCID 178603042-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

生成物 1

HCID 10253917N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-(imidazo[1,2-a]-pyridin-2-yl)benzamide収率 56%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)-phenyl]benzamide (280 mg, 0.5 mmol), 2-aminopyridine (51.8 mg, 0.55 mmol), sodium hydrogen carbonate (50 mg, 0.6 mmol) and ethanol (10 mL) was refluxed for 2 hours. After cooling, the reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=1:2) to give the title compound (130.3 mg, 45.9%) as a white solid. Then, a mixture of this solid (108 mg, 0.19 mmol), 10% Pd—C(11 mg), ethanol (8 mL) and ethyl acetate (8 mL) was stirred for 7 hours under hydrogen atmosphere. The reaction mixture was filtered and the residue obtained by evaporation of the filtrate under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=1:3) to give the title compound (18.3 mg, 20.2%) as a white solid.

後処理

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washAfter the organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=1:2)

出典と根拠

ORDレコード
ord-5d0a789c769045e9ba61ee0cb0425d0b
出典データセット
uspto-grants-2012_09
特許番号
US08263657B2

反応ノート

読み込み中…