Water → HCID 178449165, compound

HRID 1483828Notes

Reaction equation

HRID 1483828 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([NH:17][CH:18]4[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]4)[CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].O>C(Cl)Cl>[C:25]([NH:29][C@H:21]1[CH2:22][CH2:23][C@H:18]([NH:17][C:14]2[CH:15]=[CH:16][C:11]3[N:12]([C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)=[CH:9][N:10]=3)[N:13]=2)[CH2:19][CH2:20]1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 712277284-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone

Product 1

HCID 178449165HCID 178449165, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone (80 mg, 0.23 mmol) and t-Butylamine (17.2 mg, 0.23 mmol) in CH2Cl2 (1.2 mL) was added dropwise Ti(Oi-Pr)4 (0.27 mL, 0.92 mmol). The resulting mixture was stirred at room temperature overnight. LCMS showed the reaction was complete. The mixture was poured into water (150 mL) and extracted with EtOAc (100 mL*3). The organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep. HPLC to give EX. 8-78 (15 mg, 16.5%) as a white solid.

Workup

  1. extractionextracted with EtOAc (100 mL*3)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep
  6. customHPLC to give EX

Sources & evidence

ORD record
ord-099a89e9a3864606bd67e3fe61bf64c1
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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