4-Tert-Butylaniline → HCID 85890745, compound

HRID 1815211Notes

Reaction equation

HRID 1815211 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8](O)=[O:9].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:8]([C:7]2[CH:6]=[C:5]([Cl:11])[N:4]=[N:3][C:2]=2[Cl:1])=[O:9])=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 4338043,6-Dichloropyridazine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 85890745HCID 85890745, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,6-Dichloro-pyridazine-4-carboxylic acid (1.93 g, 10 mmol), 4-tert-Butyl-phenylamine (1.49 g, 10 mmol), DIEA (3.5 mL, 20 mmol), and HATU (4.56 g, 12 mmol) were added to DMF (20 mL). The reaction was stirred at rt for 15 h. The resulting dark brown solution was extracted with DCM (2×10 mL), washed with H2O (2×10 mL), and dried over sodium sulfate. The curde product was further purified using Flash Chromatography (2% MeOH/DCM), affording the desired product as yellow solid.

Workup

  1. extractionThe resulting dark brown solution was extracted with DCM (2×10 mL)
  2. washwashed with H2O (2×10 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe curde product was further purified

Sources & evidence

ORD record
ord-90d003de5a0e4b599f695071112f5b0d
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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