Trifluoroacetic acid → {2-[2-(5-benzyloxy-1H-indazol-3-yl)-1H-indol-5-yloxy]ethyl}diethylamine

HRID 1726090Notes

Reaction equation

HRID 1726090 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26](C(OC(C)(C)C)=O)[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[CH:29][CH:28]=3)=[N:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][N:9]=[C:10]2[C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([O:34][CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[CH:29][CH:28]=2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 575624245-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 136056003{2-[2-(5-benzyloxy-1H-indazol-3-yl)-1H-indol-5-yloxy]ethyl}diethylamineYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution containing 1.15 g of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester and 4 ml of trifluoroacetic acid in 5 ml of dichloromethane is stirred at 20° C. for 2 hours. The reaction mixture is evaporated under reduced pressure and the crude compound thus obtained is purified by chromatography (Nucleodur C18 column, 100-10, 250 mm×40 mm, reference No. 762020, series No. 3051181, Batch No. 2023; eluent A: water/0.07% trifluoroacetic acid, eluent B: acetonitrile/0.07% trifluoroacetic acid, gradient of composition A/B of 95%//5% to 5%/95% over 52 minutes at 75 ml/min, detection 300 nm). The fractions containing the expected compound are combined and evaporated under reduced pressure. The compound is taken up in ethyl acetate (20 ml), dried over magnesium sulfate and then evaporated under reduced pressure to obtain 320 mg of {2-[2-(5-benzyloxy-1H-indazol-3-yl)-1H-indol-5-yloxy]ethyl}diethyl-amine, which is characterized.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customthe crude compound thus obtained
  3. customis purified by chromatography (Nucleodur C18 column, 100-10, 250 mm×40 mm, reference No
  4. waiteluent A: water/0.07% trifluoroacetic acid, eluent B: acetonitrile/0.07% trifluoroacetic acid, gradient of composition A/B of 95%//5% to 5%/95% over 52 minutes at 75 ml/min, detection 300 nm)
  5. additionThe fractions containing the expected compound
  6. customevaporated under reduced pressure
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fe31a08848f24c6a8b59e36ef7138c71
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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