Diisopropylethylamine → 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-chloro-4-trifluoromethyl-phenyl)-1H-benzoimidazol-2-yl]-amide

HRID 2098239Notes

Reaction equation

HRID 2098239 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:59]2[CH:68]=[CH:67][C:62]3[NH:63][C:64]([NH2:66])=[N:65][C:61]=3[CH:60]=2)[CH:52]=[CH:53][C:54]=1[C:55]([F:58])([F:57])[F:56].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:48][C:49]1[CH:50]=[C:51]([C:59]2[CH:68]=[CH:67][C:62]3[NH:63][C:64]([NH:66][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:65][C:61]=3[CH:60]=2)[CH:52]=[CH:53][C:54]=1[C:55]([F:57])([F:58])[F:56]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27946376-Chloroimidazo[1,2-b]pyridazine-2-carboxylic acidHCID 178419691HCID 178419691, compound

Product 1

HCID 1785224796-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-chloro-4-trifluoromethyl-phenyl)-1H-benzoimidazol-2-yl]-amideYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid (600 mg), HBTU (900 mg), DIEA (1 mL) and 5-(3-chloro-4-trifluoromethyl-phenyl)-1H-benzoimidazol-2-ylamine hydrobromide salt (794 mg) in DMF (5 mL) was heated at 80° C. for 1 hour with stirring. After cooling the reaction mixture to room temperature, an aqueous sodium bicarbonate solution was added, and the mixture was stirred for 30 minutes at room temperature. The solid was filtered, washed with water, and dried under vacuum to get 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-chloro-4-trifluoromethyl-phenyl)-1H-benzoimidazol-2-yl]-amide (890 mg). LCMS (m/z): 491.8.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. stirringthe mixture was stirred for 30 minutes at room temperature
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-100d8ac0fa434f9db3e40816f479e55e
Source dataset
uspto-grants-2013_05
Patent number
US08450354B2

Reaction notes

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