Dibenzyl ether → HCID 178484195、化合物

HRID 449812ノート

反応式

HRID 449812 の反応式
C(OCC1C=CC=CC=1)C1C=CC=CC=1.C([O:23][C:24]1[CH:29]=[C:28]([O:30]CC2C=CC=CC=2)[C:27]([CH:38]([CH3:40])[CH3:39])=[CH:26][C:25]=1[C:41]1[N:42]([C:47]2[CH:48]=[C:49]3[C:53](=[CH:54][CH:55]=2)[N:52]([CH2:56][CH2:57][NH:58][CH3:59])[CH:51]=[CH:50]3)[C:43]([OH:46])=[N:44][N:45]=1)C1C=CC=CC=1>>[OH:46][C:43]1[N:42]([C:47]2[CH:48]=[C:49]3[C:53](=[CH:54][CH:55]=2)[N:52]([CH2:56][CH2:57][NH:58][CH3:59])[CH:51]=[CH:50]3)[C:41]([C:25]2[CH:26]=[C:27]([CH:38]([CH3:40])[CH3:39])[C:28]([OH:30])=[CH:29][C:24]=2[OH:23])=[N:45][N:44]=1

参加物

3

反応物 2

HCID 7657Dibenzyl etherHCID 178484196HCID 178484196、化合物

生成物 1

HCID 178484195HCID 178484195、化合物

実験手順

The benzylether [5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1-(2-(methylamino)ethyl)-1H-indol-5-yl)-4H-1,2,4-triazol-3-ol; 294 mg, 0.5 mmol) was dissolved in 6 ml degassed ethyl acetate and ethanol (1:1). 50 mg Pd/C (10%) was added and the mixture stirred under hydrogen (balloon) at rt for 6 h. After filtration the solvent was removed and the crude purified by chromatography on silica with DCM/MeOH (5-20%)/NH4OH (0.5%) to yield 203 mg (0.5 mmol) 4-(5-hydroxy-4-(1-(2-(methylamino)ethyl)-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)-6-isopropylbenzene-1,3-diol. This amine (203 mg) was added to 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid (110 mg, 0.6 mmol), EDC (154 mg, 0.8 mmol) and HOBt (108 mg, 0.8 mmol) in 9 ml DCM/DMF (2:1) at rt. The mixture was stirred for 12 h and then ethyl acetate and water added. The aq. Phase was extracted twice with ethyl acetate and the combined organic extracts washed with brine and dried over MgSO4. The crude was purified by chromatography on silica with DCM/MeOH (0-8%) to yield 133 mg (0.23 mmol) N-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol-1-yl)ethyl)-4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-methylbutanamide.

後処理

  1. dissolution294 mg, 0.5 mmol) was dissolved in 6 ml
  2. customdegassed ethyl acetate and ethanol (1:1)
  3. addition50 mg Pd/C (10%) was added
  4. filtrationAfter filtration the solvent
  5. customwas removed
  6. customthe crude purified by chromatography on silica with DCM/MeOH (5-20%)/NH4OH (0.5%)

出典と根拠

ORDレコード
ord-aa6e28d29e7646d3b3ebe2ba25b6b465
出典データセット
uspto-grants-2013_07
特許番号
US08486932B2

反応ノート

読み込み中…