4-Tert-Butylaniline → HCID 86588706, compound

HRID 2211658Notes

Reaction equation

HRID 2211658 reaction equation
Cl[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:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CN(C([O:30][N:31]1[N:39]=[N:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([NH:20][C:8]([C:7]2[CH:6]=[C:5]([Cl:11])[N:4]=[N:3][C:2]=2[O:30][N:31]2[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N:38]=[N:39]2)=[O:9])=[CH:21][CH:22]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 4338043,6-Dichloropyridazine-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 86588706HCID 86588706, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,6-dichloropyridazine-4-carboxylic acid (1.00 g, 5.18 mmol), 4-tert-butylaniline (0.92 mL, 5.60 mmol), TBTU (1.75 g, 5.44 mmol), and DIEA (1.80 mL, 10.4 mmol) in 7.5 mL of anhydrous DMF was stirred at RT under N2 overnight. The mixture was diluted with H2O, extracted with EtOAc, and the combined organic portions were washed with brine, dried with Na2SO4, filtered, and condensed. The crude compound was purified by flash column chromatography (hexanes/EtOAc/CH2Cl2, 9:0:1 to 7:2:1), to provide the desired compound as a light yellowish solid. MS (ES+): 423.0 (M+H)+. Calc'd for C21H19ClN6O2-422.87.

Workup

  1. extractionextracted with EtOAc
  2. washthe combined organic portions were washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude compound was purified by flash column chromatography (hexanes/EtOAc/CH2Cl2, 9:0:1 to 7:2:1)

Sources & evidence

ORD record
ord-62f3e95f92b7462f9cd7959bbb8c7027
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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