4-Tert-Butylaniline → HCID 85890745, compound

HRID 2247299Notes

Reaction equation

HRID 2247299 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-148bab1818284088b13ac7b9c80585a3
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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