Dibenzyl ether → HCID 178484195、化合物

HRID 449814ノート

反応式

HRID 449814 の反応式
[CH2:1](OCC1C=CC=CC=1)C1C=CC=CC=1.[NH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([N:28]3[C:32]([C:33]4[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[C:36]([O:42]CC5C=CC=CC=5)=[CH:35][C:34]=4[O:50]CC4C=CC=CC=4)=[N:31][N:30]=[C:29]3[OH:58])=[CH:25][CH:26]=2)[CH:21]=[CH:20]1>>[OH:58][C:29]1[N:28]([C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][CH:25]=2)[N:19]([CH2:18][CH2:17][NH:16][CH3:1])[CH:20]=[CH:21]3)[C:32]([C:33]2[CH:38]=[C:37]([CH:39]([CH3:40])[CH3:41])[C:36]([OH:42])=[CH:35][C:34]=2[OH:50])=[N:31][N:30]=1

参加物

3

反応物 2

HCID 7657Dibenzyl etherHCID 178438831HCID 178438831、化合物

生成物 1

HCID 178484195HCID 178484195、化合物

実験手順

The benzylether [4-(1-(2-aminoethyl)-1H-indol-5-yl)-5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4H-1,2,4-triazol-3-ol; 188 mg, 0.33 mmol) was dissolved in 6 ml degassed THF/methanol (1:1). 50 mg Pd/C (10%) was added and the mixture stirred under hydrogen (balloon) at rt for 5 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 71 mg (0.18 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 (50 mg, 0.125) was added to 4-(2,5-dioxopyrrolidin-1-yl)butanoic acid (26 mg, 0.14 mmol), EDC (38 mg, 0.2 mmol) and HOBt (27 mg, 0.2 mmol) in 1.5 ml DMF 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 (3-10%) to yield 34 mg (0.061 mmol) product.

後処理

  1. dissolution188 mg, 0.33 mmol) was dissolved in 6 ml
  2. customdegassed THF/methanol (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-ceb69c6ba5b94bb6a5ba288d2f8efe51
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…