Dibenzyl ether → HCID 178484195, 화합물

HRID 1428634노트

반응식

HRID 1428634 반응식
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

참가 물질

3

반응물 2

HCID 7657Dibenzyl etherHCID 178484196HCID 178484196, 화합물

생성물 1

HCID 178484195HCID 178484195, 화합물

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-8367f046b83a4196a40085446add7ec0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937094B2

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