Trifluoroacetic acid → HCID 11517360, compound

HRID 1723834Notes

Reaction equation

HRID 1723834 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[CH:20]=[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]3=[CH:17][C:16]=2[C:15]2=[N:26][N:27](C(OC(C)(C)C)=O)[C:28]([CH3:29])=[C:14]2[C:13]1=[O:37])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[CH:20]=[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]3=[CH:17][C:16]=2[C:15]2=[N:26][NH:27][C:28]([CH3:29])=[C:14]2[C:13]1=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57559685HCID 57559685, compound

Product 1

HCID 11517360HCID 11517360, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-{3-[(tert-butoxycarbonyl)amino]propyl}-3-methyl-4-oxo-4,5-dihydro-2H-benzo[g]pyrazolo[4,3-c]quinoline-2-carboxylate (1-7) (0.14 g, 0.28 mmol, 1.0 equiv) in CH2Cl2 (6 ml) was added trifluoroacetic acid (3 ml) and the reaction was stirred at room temperature for 4 hours. The solvent was evaporated under reduced pressure and the residue was dissolved DMSO/NH4HO and purified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.05% NH4OH present) to yield 5-(3-aminopropyl)-3-methyl-2,5-dihydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-8) as a white solid. 1H NMR (500 MHz, MeOH-d4, TFA Salt) δ 8.65 (s, 1H), 8.00 (m, 2H), 7.97 (s, 1H) 7.57 (t, 1H), 7.52 (t, 1H), 4.57 (t, 2H), 3.06 (t, 2H), 2.69 (s, 3H), 2.26 (t, 2H). LRMS m/z (M+H) 307.5 found, 307.2 required.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved DMSO/NH4HO
  3. custompurified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.05% NH4OH present)

Sources & evidence

ORD record
ord-e374f25843a045bd9dc173a241ab4b78
Source dataset
uspto-grants-2009_02
Patent number
US07485649B2

Reaction notes

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