Pyridine → HCID 178520812, compound

HRID 1483844Notes

Reaction equation

HRID 1483844 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([NH:17][C@H:18]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]4)[CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[Cl:31][CH2:32][C:33](Cl)=[O:34].C([O-])(O)=O.[Na+]>C(Cl)Cl.CO>[Cl:31][CH2:32][C:33]([NH:24][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)=[O:34]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 178511600HCID 178511600, compound

Product 1

HCID 178520812HCID 178520812, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of trans-N1-(3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)cyclohexane-1,4-diamine (90 mg, 0.26 mmol) and pyridine (0.08 mL, 1.04 mmol) in CH2Cl2 (2.6 mL) was added dropwise chloroacetyl chloride (0.03 mL, 0.39 mmol). The resulting mixture was stirred at room temperature overnight. TLC (CH2Cl2:MeOH=10:1) showed the reaction was complete. The mixture was poured into sat. aq. NaHCO3 (100 mL) and extracted with EtOAc (50 mL*3). The extracts were dried over Na2SO4, filtered and concentrated in vacuo to give crude 2-chloro-N-(trans-4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexyl)acetamide (110 mg, 101%) as a yellow solid.

Workup

  1. extractionextracted with EtOAc (50 mL*3)
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-284a8dae910947a688ae018848b67a22
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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