Trifluoroacetic acid → (E)-4-(2-(2-(3-Methoxyquinolin-2-yl)vinyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoic acid

HRID 718679Notes

Reaction equation

HRID 718679 reaction equation
[CH3:1][O:2][C:3]1[C:4](/[CH:13]=[CH:14]/[C:15]2[N:16]=[C:17]3[C:22]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:20]=[N:19][N:18]3[C:29]=2[C:30]2[CH:42]=[CH:41][C:33]([C:34]([O:36]C(C)(C)C)=[O:35])=[CH:32][CH:31]=2)=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4](/[CH:13]=[CH:14]/[C:15]2[N:16]=[C:17]3[C:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[CH:21][CH:20]=[N:19][N:18]3[C:29]=2[C:30]2[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:41][CH:42]=2)=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117732520(E)-tert-Butyl 4-(2-(2-(3-methoxyquinolin-2-yl)vinyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

Product 1

HCID 117728377(E)-4-(2-(2-(3-Methoxyquinolin-2-yl)vinyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 63a (212 mg, 1.22 mmol) in 3 mL of DCM at rt was added TFA (1.00 mL, 13.1 mmol). After stirring at rt for 0.5 h, the mixture was concentrated in vacuo and the residue was triturated with DCM to give a red solid. Recrystallization of the solid in 1:1 MeOH/DCM afforded the title compound 119 as a red solid. 1H NMR (DMSO-d6, 400 MHz): δ=8.09-8.22 (m, 2H), 8.00 (s, 1H), 7.77-7.93 (m, 3H), 7.44-7.59 (m, 2H), 6.43 (d, J=5.6 Hz, 1H), 5.99 (d, J=6.1 Hz, 2H), 5.81 (s, 1H), 5.71 (s, 1H), 4.06 (br. s., 4H), 3.99 (s, 3H), 3.86 ppm (br. s., 4H). Mass spectrum (ESI, m/z): Calcd. for C29H25N5O4, 508.2 (M+H). found 508.5.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was triturated with DCM
  3. customto give a red solid
  4. customRecrystallization of the solid in 1:1 MeOH/DCM

Sources & evidence

ORD record
ord-b0a56c8b4a4c4c33bb800be14c8da6fe
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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