Diisopropylethylamine → HCID 178522477, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[N:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Br.[Cl:48][C:49]1[CH:50]=[C:51]([C:55]2[CH:64]=[CH:63][C:58]3[NH:59][C:60]([NH2:62])=[N:61][C:57]=3[CH:56]=2)[CH:52]=[CH:53][CH:54]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:48][C:49]1[CH:50]=[C:51]([C:55]2[CH:64]=[CH:63][C:58]3[NH:59][C:60]([NH:62][C:11]([C:9]4[N:10]=[C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][N:6]5[CH:8]=4)=[O:13])=[N:61][C:57]=3[CH:56]=2)[CH:52]=[CH:53][CH:54]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid (400 mg), HBTU (900 mg) and DIEA (1 mL) in DMF (5 mL) was heated at 80° C. for 10 minutes. To this reaction mixture 5-(3-chlorophenyl)-1H-benzoimidazol-2-ylamine hydrobromide salt (265 mg) was added, and the mixture was heated at 80° C. for 30 minutes. After cooling the reaction mixture to room temperature, an aqueous sodium bicarbonate solution was added, and the mixture was stirred for 30 minutes. The mixture was filtered, washed with water, and purified on silica gel column to obtain 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-chloro-phenyl)-1H-benzoimidazol-2-yl]-amide (635 mg). LC-MS (m/z). 423.7.
Workup
- temperaturethe mixture was heated at 80° C. for 30 minutes
- temperatureAfter cooling the reaction mixture to room temperature
- filtrationThe mixture was filtered
- washwashed with water
- custompurified on silica gel column
Sources & evidence
- ORD record
- ord-6ef6f1f3dc7345f9b56d36de2ca8862e
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450354B2
Reaction notes
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