Trifluoroacetic acid → 8-Morpholino-3-(6-(piperazin-1-yl)pyridin-3-yl)-N-(quinolin-2-yl)imidazo[1,2-b]pyridazine-2-carboxamide trifluoroacetate salt

HRID 718596Notes

Reaction equation

HRID 718596 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:29]4[CH:30]=[CH:31][C:32]([N:35]5[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]5)=[N:33][CH:34]=4)=[C:14]([C:16](=[O:28])[NH: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:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]>C(Cl)Cl>[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:29]4[CH:34]=[N:33][C:32]([N:35]5[CH2:36][CH2:37][NH:38][CH2:39][CH2:40]5)=[CH:31][CH:30]=4)=[C:14]([C:16]([NH: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)=[O:28])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117732470tert-Butyl 4-(5-(8-morpholino-2-(quinolin-2-ylcarbamoyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 1177285258-Morpholino-3-(6-(piperazin-1-yl)pyridin-3-yl)-N-(quinolin-2-yl)imidazo[1,2-b]pyridazine-2-carboxamide trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 20d (191 mg, 0.300 mmol) was placed in an 8 mL vial equipped with a stir bar and then DCM (4 mL) was added. Once the solution was homogeneous, TFA (1 mL) was added dropwise. The mixture was stirred at rt for 4 h. The solvent was removed under reduced pressure. The residue was dissolved in DCM (10 mL) and then the solvent was removed under reduced pressure again. The residue was triturated with Et2O (20 mL), resulting in a yellow precipitate, which was isolated by filtration and washed with Et2O (2×10 mL). The residual solvent was removed under reduced pressure to afford the title compound 3. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 10.35 (s, 1H), 8.78 (br. s., 2H), 8.50 (d, J=2.2 Hz, 1H), 8.41 (d, J=9.0 Hz, 1H), 8.35 (d, J=9.0 Hz, 1H), 8.21 (d, J=5.9 Hz, 1H), 7.92-8.00 (m, 2H), 7.89 (d, J=8.6 Hz, 1H), 7.70-7.79 (m, 1H), 7.48-7.58 (m, 1H), 7.07 (d, J=9.0 Hz, 1H), 6.50 (d, J=5.9 Hz, 1H), 4.04-4.16 (m, 4H), 3.80-3.91 (m, 8H), 3.20-3.29 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H29N9O2: 536.3 (M+H). Found: 536.3.

Workup

  1. customvial equipped with a stir bar
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. customthe solvent was removed under reduced pressure again
  5. customThe residue was triturated with Et2O (20 mL)
  6. customresulting in a yellow precipitate
  7. customwhich was isolated by filtration
  8. washwashed with Et2O (2×10 mL)
  9. customThe residual solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c567c681ec4e494e8cd1056d52492332
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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