Trifluoroacetic acid → HCID 505774, compound

HRID 1756596Notes

Reaction equation

HRID 1756596 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:30]=[C:29]3[C:17]([C:18](=[O:32])[C:19]4[N:28]3[C:27](=[O:31])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=4)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO>[N:11]1([C:14]2[CH:30]=[C:29]3[C:17]([C:18](=[O:32])[C:19]4[N:28]3[C:27](=[O:31])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=4)=[CH:16][CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 478666HCID 478666, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 505774HCID 505774, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9-(4-t-butyloxycarbonylpiperazinyl)indolo[2,1-b]quinazoline-6,12-dione (Example 52, 40 mg, 925 μmol) in 1 mL of methylene chloride was added 1 mL of trifluoroacetic acid (TFA). After 30 min, saturated sodium bicarbonate was added. The aqueous layer was separated and extracted with 3×50 mL of chloroform, dried over anhydrous sodium sulfate, filtered and solvent removed in vacuo to give 37 mg of crude product. Silica gel chromatorgraphy using (95:5) methylene chloride:methanol as eluent gave 24 mg (77%) of the title compound: mp 214° C. (dec); 1H NMR(DMSO-d6) δ 2.5 (s, 4H), 3.5 (s, 4H), 6.88-6.94 (dd, 1H), 7.62-7.66 (d, 1H), 7.68-7.75 (m, 1H), 7.90-7.94 (m, 2H), 7.95-7.98 (m, 1H), 8.26-8.31 (d, 1H).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with 3×50 mL of chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customto give 37 mg of crude product

Sources & evidence

ORD record
ord-9104be2be56945c58a222c8018ea1673
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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