Trifluoroacetic acid → 4-(8-Morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)benzoic acid trifluoroacetate

HRID 718675Notes

Reaction equation

HRID 718675 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:40]=[CH:39][C:31]([C:32]([O:34]C(C)(C)C)=[O:33])=[CH:30][CH:29]=4)=[C:14]([CH2:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=5[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>C(Cl)Cl>[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:39][CH:40]=4)=[C:14]([CH2:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=5[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117732518tert-Butyl 4-(8-morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

Product 1

HCID 1177285874-(8-Morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)benzoic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 60b (55.0 mg, 0.102 mmol) in DCM (2 mL) at RT was added TFA (500 μL, 6.53 mmol). After stirring at rt for 0.5 h, the mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0:1-1:9 MeOH-DCM) to afford the title compound 79 (with 1.1 eq TFA) as a white solid. 1H-NMR (CDCl3; 400 MHz) δ: 8.03 (d, J=8.6 Hz, 2H), 8.00 (d, J=5.6 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.56-7.62 (m, 2H), 7.15 (d, J=8.1 Hz, 1H), 6.11 (d, J=5.6 Hz, 1H), 3.87-4.05 (m, 8H), 3.57 (t, J=7.1 Hz, 2H), 3.34-3.43 (m, 2H), 3.07-3.18 (m, 2H), 2.71-2.83 (m, 2H), 1.77-1.95 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C28H29N5O3, 484.2 (M+H). found 484.5.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (0:1-1:9 MeOH-DCM)

Sources & evidence

ORD record
ord-163cf1b66a6f4c63bd9239bf4a19710f
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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