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Hydrochloric Acid → (Rac)-2-(4-{3-[1-(3-methyl-3h-benzoimidazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazin-6-yl}-pyrazol-1-yl)-ethanol

HRID 69228
Notes
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Reaction equation

HRID 69228 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([CH:11]([C:13]3[N:17]4[N:18]=[C:19]([C:22]5[CH:23]=[N:24][N:25]([CH2:27][CH2:28][O:29]C6CCCCO6)[CH:26]=5)[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH3:12])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.Cl>C(Cl)Cl.CO.O1CCOCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([CH:11]([C:13]3[N:17]4[N:18]=[C:19]([C:22]5[CH:23]=[N:24][N:25]([CH2:27][CH2:28][OH:29])[CH:26]=5)[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH3:12])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68633396(Rac)-3-[1-(3-methyl-3h-benzoimidazol-5-yl)-ethyl]-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1h-pyrazol-4-yl}-imidazo[1,2-b]pyridazine

Product 1

HCID 57917436(Rac)-2-(4-{3-[1-(3-methyl-3h-benzoimidazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazin-6-yl}-pyrazol-1-yl)-ethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

(rac)-3-[1-(3-Methyl-3H-benzoimidazol-5-yl)-ethyl]-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazine (Stage 185.1, 600 mg, 1.018 mmol) was dissolved in DCM (10 mL) and MeOH (2.5 mL). HCl in dioxane (4 N, 1.272 mL) was added and the RM was stirred 1 h at rt. The solvent was totally evaporated and the residue taken in water /acetonitrile. It was basified with NaHCO3. the mixture was cooled down with dry ice and sonicated to afford a suspension. It was filtered and collected, and dried under high vacuum overnight to afford the title compound as a white solid (tR 2.04 min (conditions 8), MH+=388, 1H-NMR in DMSO-d6: 8.39 (s, 1H); 8.07 (d, 2H); 8.01 (d, 1H); 7.69 (s, 1H); 7.61 (s, 1H); 7.51 (d, 1H); 7.47 (d, 1H); 7.23 (d, 1H); 4.95 (t, 1H); 4.76 (q, 1H); 4.18 (t, 2H); 3.78 (s, 3H); 3.75 (q, 2H); 1.79 (d, 3H)).

Workup

  1. customThe solvent was totally evaporated
  2. temperaturethe mixture was cooled down with dry ice
  3. customsonicated
  4. customto afford a suspension
  5. filtrationIt was filtered
  6. customcollected
  7. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-4968c7be8dac4a4bb928fde6ecf62a9b
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822468B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes