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

HRID 2384368노트

반응식

HRID 2384368 반응식
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

참가 물질

5

반응물 3

HCID 104392-AminopyridineHCID 516892Sodium Bicarbonate2회HCID 178603042-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5d0a789c769045e9ba61ee0cb0425d0b
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263657B2

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