Methyl chloroformate → (rac)-4-{3-[1-(5,7-Difluoro-quinolin-6-yl)-ethyl]-imidazo[1,2-b]pyridazin-6-yl}-piperazine-1-carboxylic acid methyl ester

HRID 1942072Notes

Reaction equation

HRID 1942072 reaction equation
[F:1][C:2]1[C:11]([CH:12]([C:14]2[N:18]3[N:19]=[C:20]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH3:13])=[C:10]([F:29])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl[C:31]([O:33][CH3:34])=[O:32]>N1C=CC=CC=1>[CH3:34][O:33][C:31]([N:26]1[CH2:27][CH2:28][N:23]([C:20]2[CH:21]=[CH:22][C:17]3[N:18]([C:14]([CH:12]([C:11]4[C:2]([F:1])=[C:3]5[C:8](=[CH:9][C:10]=4[F:29])[N:7]=[CH:6][CH:5]=[CH:4]5)[CH3:13])=[CH:15][N:16]=3)[N:19]=2)[CH2:24][CH2:25]1)=[O:32]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 50914336(rac)-5,7-Difluoro-6-[1-(6-piperazin-1-yl-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-quinoline

Product 1

HCID 50914493(rac)-4-{3-[1-(5,7-Difluoro-quinolin-6-yl)-ethyl]-imidazo[1,2-b]pyridazin-6-yl}-piperazine-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(rac)-5,7-Difluoro-6-[1-(6-piperazin-1-yl-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-quinoline (Example 6, 35 mg, 0.089 mmol) was dissolved in pyridine (0.89 mL) and methyl chloroformate (0.010 mL, 0.133 mmol) was added. The RM was stirred at RT for 1.5 h. The mixture was concentrated and the residue was purified by flash chromatography and afforded the title compound as a beige foam (tR 3.70 min (conditions 1), MH+=453).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8e4835ca268647eba4f876c7d60c147e
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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