Hydrochloric Acid → 1-(3-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-piperidin-4-one

HRID 69177Notes

Reaction equation

HRID 69177 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[CH:13][C:14]4[N:15]([C:17]([CH2:20][C:21]5[CH:22]=[C:23]6[C:28](=[CH:29][CH:30]=5)[N:27]=[CH:26][CH:25]=[CH:24]6)=[CH:18][N:19]=4)[N:16]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[N:27]1[C:28]2[C:23](=[CH:22][C:21]([CH2:20][C:17]3[N:15]4[N:16]=[C:11]([N:8]5[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]5)[CH:12]=[CH:13][C:14]4=[N:19][CH:18]=3)=[CH:30][CH:29]=2)[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 579173276-[6-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-imidazo[1,2-b]pyridazin-3-yl methyl]-quinoline

Product 1

HCID 579172371-(3-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-piperidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-[6-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-imidazo[1,2-b]pyridazin-3-yl methyl]-quinoline (Example 110, 132 mg, 0.329 mmol) was dissolved in THF (493 μL). A 2 M HCl solution (493 μL) was then added and the RM was stirred at rt for 22 h and then at 40° C. for 3 h. A basic work up (KHCO3) followed by a crystallization in Et2O/isopropanol afforded the title compound as white crystals (tR 1.33/1.48 min (conditions 6), MH+=358.1, 1H-NMR in DMSO-d6: 8.84 (m, 1H); 8.29 (m, 1H); 7.90 (m, 3H); 7.72 (m, 1H); 7.49 (m, 2H); 7.22 (d, 1H); 4.42 (s, 2H); 3.85 (m, 4H); 2.35 (m, 4H)).

Workup

  1. waitat 40° C. for 3 h
  2. customA basic work up (KHCO3) followed by a crystallization in Et2O/isopropanol

Sources & evidence

ORD record
ord-359736c4bb3a4c8387c98829a69f63f5
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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