Trifluoroacetic acid → (E)-5-(8-Morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)picolinic acid trifluoroacetate

HRID 718677Notes

Reaction equation

HRID 718677 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:29]=[CH:30][C:31]([C:34]([O:36]C(C)(C)C)=[O:35])=[N:32][CH:33]=4)=[C:14](/[CH:16]=[CH: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:34]([OH:36])=[O:35])=[N:32][CH:33]=4)=[C:14](/[CH:16]=[CH: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 117732519(E)-tert-Butyl 5-(8-morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)picolinate

Product 1

HCID 117728354(E)-5-(8-Morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)picolinic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 61b (200 mg, 0.371 mmol) in 5 mL of DCM at rt was added TFA (2.00 mL, 26.1 mmol). After stirring at rt for 6 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 107 (with 1 eq of TFA) as a bright yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 8.97 (br. s., 1H), 8.35 (br. s., 2H), 7.88-8.05 (m, 2H), 7.65-7.79 (m, 2H), 7.51-7.65 (m, 1H), 6.16 (d, J=5.6 Hz, 1H), 4.09 (br. s., 4H), 3.90-4.03 (m, 4H), 3.19 (br. s., 2H), 2.84 (br. s., 2H), 1.93 (br. s., 2H), 1.78-1.89 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C27H26N6O3, 483.5 (M+H). found 483.4.

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-bce3e67ac8c6441282df977d10edfdad
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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