Water → HCID 71235302, compound

HRID 1483842Notes

Reaction equation

HRID 1483842 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([C:7]([OH:10])([CH3:9])[CH3:8])[CH2:3]1.Cl[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)=[CH:19][N:20]=2)[N:17]=1.[F-].[K+].O>CS(C)=O>[Cl:27][C:23]1[CH:22]=[C:21]([C:18]2[N:16]3[N:17]=[C:12]([NH:1][C@H:2]4[CH2:6][CH2:5][C@H:4]([C:7]([OH:10])([CH3:9])[CH3:8])[CH2:3]4)[CH:13]=[CH:14][C:15]3=[N:20][CH:19]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 574186866-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazineHCID 89389893HCID 89389893, compound

Product 1

HCID 71235302HCID 71235302, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(trans-3-aminocyclopentyl)propan-2-ol (82 mg, 0.57 mmol), 6-chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine (100 mg, 0.38 mmol) and KF (66.2 mg, 1.14 mmol) in DMSO (1 mL) was stirred at 130° C. overnight. LCMS showed the reaction was complete. The mixture was poured into water (100 mL) and extracted with EtOAc (50 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to give EX. 8-82 (45 mg, 32%) as an off-white solid.

Workup

  1. extractionextracted with EtOAc (50 mL*3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC
  6. customto give EX

Sources & evidence

ORD record
ord-91a1b69a4ff741b4b8bbba946e584dc5
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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