Triethylamine → HCID 57802546, compound

HRID 2102415Notes

Reaction equation

HRID 2102415 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([NH:17][NH2:18])=[O:16])=[N:13][N:12]3[CH:19]=[CH:20][N:21]=[C:11]3[CH:10]=2)=[C:4]([F:22])[CH:3]=1.BrC1C=C[C:27]([NH:30]C2C(C(O)=O)=NN3C=CN=C3C=2)=C(F)C=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.NN.CCN(CC)CC>CC(N(C)C)=O.CCOC(C)=O>[NH2:30][C:27]1[O:16][C:15]([C:14]2[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[F:22])=[CH:10][C:11]3[N:12]([CH:19]=[CH:20][N:21]=3)[N:13]=2)=[N:17][N:18]=1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 9321HydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 595193857-(4-Bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acidHCID 69006850HCID 69006850, compound

Product 1

HCID 57802546HCID 57802546, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

Preparation of 7-(4-bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acid hydrazide: A mixture of 7-(4-bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acid (1.00 equiv), EDCI (1.50 equivalents), and HOBt (1.50 equivalents) in DMA is stirred for 30 minutes at room temperature under N2. Hydrazine (3.00 equivalents) is added followed by Et3N (2.50 equivalents). After the reaction mixture is stirred for 16 hours at room temperature, it is diluted with EtOAc and washed with saturated NH4Cl solution, saturated NaHCO3 solution and saturated NaCl. The organic layer is dried (Na2SO4) and concentrated under reduced pressure to yield the desired product. The product may be purified by flash column chromatography if further purification is necessary.

Workup

  1. stirringAfter the reaction mixture is stirred for 16 hours at room temperature
  2. washwashed with saturated NH4Cl solution, saturated NaHCO3 solution and saturated NaCl
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afa3e6fd081d498d9962f0afce73ba1b
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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