Trifluoroacetic acid → (E)-4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoic acid trifluoroacetic acid salt

HRID 718572Notes

Reaction equation

HRID 718572 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](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=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](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=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 117732458(E)-tert-Butyl 4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

Product 1

HCID 117728839(E)-4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoic acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of compound 5g (0.26 g, 0.49 mmol) in DCM (8 mL) was added TFA (2 mL). The solution was stirred at rt for 3 h, and concentrated to obtain a residue that was washed with Et2O (3×20 mL) and isolated as a yellow solid, compound 40. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.52-8.63 (m, 1H), 8.11-8.24 (m, 4H), 8.01-8.11 (m, 2H), 7.79-7.98 (m, 5H), 7.61-7.75 (m, 1H), 6.49 (d, J=5.6 Hz, 1H), 4.11 (br. s., 4H), 3.83-3.96 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H23N5O3: 478.2 (M+H). Found 478.1.

Workup

  1. concentrationconcentrated
  2. customto obtain a residue that
  3. washwas washed with Et2O (3×20 mL)

Sources & evidence

ORD record
ord-6f76d248e51c4ab9832fcd478efb37fa
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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