Trifluoroacetic acid → HCID 59300889, compound

HRID 2235445Notes

Reaction equation

HRID 2235445 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:32][C:12]3=[CH:13][C:14]4[C:15]([CH3:31])([CH3:30])[C:16](=[O:29])[N:17]([CH2:20][C:21](=[O:28])[C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:18]=4[CH:19]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>>[OH:28][CH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][N:17]1[C:18]2[CH:19]=[C:11]3[N:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[NH:32][C:12]3=[CH:13][C:14]=2[C:15]([CH3:31])([CH3:30])[C:16]1=[O:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59300869HCID 59300869, compound

Product 1

HCID 59300889HCID 59300889, compoundYield 45.2%

Procedure

To a mixture of 2-(4-methoxy-phenyl)-7,7-dimethyl-5-(2-oxo-2-phenyl-ethyl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (33 mg) and trifluoroacetic acid (77 μl) is added drop-wise SiEt3 (30 μl) at RT for 48 h. The mixture is concentrated in vacuo and the residue is taken-up in MeOH (5 ml), CH2Cl2 (5 ml) and saturated NaHCO3 solution. The resulting solution is stirred at RT for 30 min, neutralized with hydrochloric acid (1 N) and extracted with CH2Cl2. The organic layer is washed with water, dried over MgSO4 and evaporated. The desired compound (15 mg) is obtained by preparative RP-HPLC, eluted with a water/MeCN gradient.

Workup

  1. additionis added drop-wise SiEt3 (30 μl) at RT for 48 h
  2. concentrationThe mixture is concentrated in vacuo
  3. extractionextracted with CH2Cl2
  4. washThe organic layer is washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-0d0e102f6541442cbcdd6ec43e046865
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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