Hydrochloric Acid → 4-[6-Chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazin-3-yl]pyrid-2-ylamine

HRID 80729Notes

Reaction equation

HRID 80729 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24]C(=O)OC(C)(C)C)[CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)[N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59406969tert-Butyl {4-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazin-3-yl]pyrid-2-yl}carbamate

Product 1

HCID 594069504-[6-Chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazin-3-yl]pyrid-2-ylamineYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.76 g (1.67 mmol) of tert-butyl {4-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-b]pyridazin-3-yl]pyrid-2-yl}carbamate in 8 mL of dichloromethane are added 4 mL (48 mmol) of hydrochloric acid. After stirring for 2 hours at room temperature, the solvent is evaporated off under reduced pressure, the oily residue is taken up with aqueous ammonia and the product is extracted with dichloromethane. The organic phase is filtered on a hydrophobic cartridge and concentrated under reduced pressure. The solid obtained is triturated with diisopropyl ether to give 0.56 g of solid after filtering off and drying under reduced pressure.

Workup

  1. customthe solvent is evaporated off under reduced pressure
  2. extractionthe product is extracted with dichloromethane
  3. filtrationThe organic phase is filtered on a hydrophobic cartridge
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. customis triturated with diisopropyl ether

Sources & evidence

ORD record
ord-ec4f98bd8a074ed3ad7c9945ae5d4810
Source dataset
uspto-grants-2014_09
Patent number
US08846676B2

Reaction notes

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