Water → HCID 178459250, compound

HRID 1483824Notes

Reaction equation

HRID 1483824 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[NH2:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]1.[F-].[K+].O>CS(C)=O>[Cl:17][C:13]1[CH:12]=[C:11]([C:8]2[N:6]3[N:7]=[C:2]([NH:18][CH2:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([C:26]([OH:29])([CH3:27])[CH3:28])[CH2:22][CH2:21]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 574186866-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazineHCID 178459251HCID 178459251, compound

Product 1

HCID 178459250HCID 178459250, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine (100 mg, 0.38 mmol), 2-(trans-4-(aminomethyl)cyclohexyl)propan-2-ol (140 mg, 0.76 mmol) and KF (51 mg, 0.88 mmol) in DMSO (2 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. 8-76 (12 mg, 8%) as a yellow 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-741431df80724d949f370a1be2848c23
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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